BOC-(RS)-3-AMINO-1,2-PROPANEDIOL

3 g (1.0 eq., 32.93 mmol) of the 3-amino-1, 2-propane diol 23 was dissolved in 20 mL of tert-BuOH and 20 mL of 1 M NaOH, and under ice cooling, added with 20 mL of tert-BuOH solution containing 7.19 g (1.0 eq., 32.93 mmol) of Boc1-aminopropane-2, 3-diol (5 g, 55 mmol) was dissolved in methanol (200 ml) followed by dropwise addition of triethylamine (0.5 ml per mmol of amine) and di-tert-butyl dicarbonate [(BOC)2O] wherein BOC corresponds to tertbutyloxycarbonyl (17.97 g, 82 mmol). The reaction medium was heated at 40-50° C. for 20 min then stirred at room temperature for 1 hour. After evaporation of the solvent, the colorless oily residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 95:5) to give the desired compound in the form of a colorless oil which crystallized slowly. Yield: 99percent Rf (dichloromethane/methanol 9:1): 0.39 IR: νNH 3350 cmExample 22; Preparation of 1-amino-2, 3-di(tetradecylthioacetylthio)propane hydrochloride; Preparation of 1-(tert-butyloxycarbonylamino)propane-2, 3-diol (example 22a); 1-aminopropane-2, 3-diol (5 g, 55 mmol) was dissolved in methanol (200 ml) followed by dropwise addition of triethylamine (0.5 ml per mmol of amine) and di-tert-butyl dicarbonate [(BOC)2O] (wherein BOC corresponds to tertbutyloxycarbonyl) (17.97 g, 82 mmol). The reaction medium was heated at 40-50° C. for 20 min then stirred at room temperature for 1 hour. After evaporation of the solvent, the colorless oily residue was purified by chromatography on silica gel (eluent : dichloromethane/methanol 95:5) to give the desired compound in the form of a colorless oil which crystallized slowly. Yield: 99percent Rf (dichloromethane/methanol 9:1): 0.39 IR: vNH 3350 cmPreparation of 1-(tert-butyloxycarbonylamino)propane-2, 3-diol (example 17a) Step 1 Intermediate A1A: tert-Butyl(2, 3-dihydroxypropyl)carbamate (+/-)-3-amino-1, 2-propanediol (11.29 g, 124 mmol) was dissolved in CH2Cl2:CH3OH (1:5) (1 M) and triethylamine (2 mL, 14.7 mmol) was added. Di-tert-butyl dicarbonate (32.5 g, 149 mmol) was dissolved in dichloromethane (0.8 M, 186 mL) and added slowly to the reaction mixture. The resulting reaction was stirred at 23 °C for 2 h, followed by TLC analysis that showed a full consumption of the starting material. The reaction mixture was evaporated under reduced pressure, and the residue was purified by column chromatography with EtOA/:Hexanes 1:4, then dried on high vacuum to yield 11 as a white solid (23.7 g, 94 percent yield). 1H NMR (500 MHz, CDCl3) δ 5.28 – 4.96 (m, 1H), 3.83 – 3.73 (m, 1H), 3.60 (qd, J = 11.7, 4.9 Hz, 2H), 3.44 (s, 1H), 3.27 (dt, J = 12.9, 6.0 Hz, 2H), 1.46 (s, 9H). 13C NMR (126 MHz, CDCl3) δ 157.45 , 80.13 , 71.37 , 63.58, 28.35 , 27.42.Step 2 tert-Butyl 2-oxoethylcarbamate: Sodium periodate (41.52 g; 194 mmol; 1.00 equiv) was added in several batches to To a solution of N-Boc-3-aminopropane-1, 2-diol (191 mg, 1.0 mmol) in water (10 mL) was added sodium periodate (255 mg, 1.2 mmol). The mixture was then stirred rapidly for 2 hours. Work-up via dichloromethane extraction gave the crude aldehyde, which was used directly in the next step without further purification.11 (10 g, 52 mmol) was suspended in H2O (0.6M, 87.2mL) and the flask was covered in foil (to protect NaIO4 from light). NaIO4 (13.4 g, 62.8 mmol) was then added and the reaction was stirred for 1 h. A white precipitate had formed after 1 h, and TLC analysis showed full consuption of the starting material. The precipitate was filtered off, and the aqueous layer was extracted with CHCl3 (8x50 mL). The organic layer was dried with MgSO4, filtered, and evaporated to yield 12 as a yellow oil, which was used immediately without further purification (7.7g, 93% yield). 1H NMR (500 MHz, CDCl3) delta 9.68 (s, 1H), 5.23 (s, 1H), 4.10 (d, J = 5.2 Hz, 2H), 1.47 (s, 9H). 13C NMR (126 MHz, CDCl3) delta 197.21, 155.67, 80.19, 51.39, 28.28.This general procedure can also be used to prepare the N-(boc)- aminoacetaldehyde suitable for use without further purification. Generally however, for the N-[boc-(3-Amino)]-1 , 2-propanediol, only DCM is used in the reaction (not a mix of ethyl acetate and DCM) in roughly the same total concentration of organic to aqueous (ice) except that the reaction is not allowed to warm to RT and is always kept cold by precooling the extraction mixtures. The N-(boc)-aminoacetaldehyde can be used in a reductive amination to make the N-boc protected backbone ester, whereas the N-(Fmoc)- aminoacetaldehyde can be used in the reductive amination to prepare the N-Fmoc protected backbone ester.56g of hexadecanoic acid (0.22mol), 19.1 g of N-Boc-2, 3-dihydroxypropylamine (0.1 mol) was added to a 500 mL reaction flask, 300 mL of dichloromethane was added, and after stirring well, 27.8 g of N, N'-diisopropylcarbodiimide ( DIC) (0.22mol) and 0.2g of 4-dimethylaminopyridine (DMAP). After stirring at room temperature for 24 hours, it was filtered. The solid obtained after rotary distillation of the filtrate was further recrystallized and purified to obtain 62 g of intermediate product. This step The yield was 92.8%.Add all the obtained intermediate products to a 250 mL reaction flask, add 150 mL of dichloromethane, stir well and add 20% by volume of trifluoroacetic acid, react at room temperature for 5 hours, and then recrystallize after removing the solvent by rotary distillation to obtain 51 g of the final product. . The yield in this step is 96.8%.Weigh 700 mg of monocarboxylated and alkylated oxaliplatin and dissolve it in 5 ml of dichloromethane.Add 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride 191mg, 140mg of 4-dimethylaminopyridine, stirred at 25 C for 2h to activate the reaction, Then 30 mg of tert-butyl N- (2, 3-dihydroxypropyl) carbamate was added, and the reaction was carried out for 48 hours.Rotary evaporation and concentration, redissolved in a trifluoroacetic acid / dichloromethane (volume ratio = 1/1) mixed solvent to continue the reaction for 4h, then concentrated by rotary evaporation, precipitated with ether, and dried in vacuo, The dialkylated oxaliplatin precursor DiPt is obtained.The obtained material was characterized by nuclear magnetic resonance hydrogen spectrum and mass spectrum, and the results are shown in FIG. 1.Boc-(RS)-3-amino-1, 2-propanediol solution was prepared by adding Boc-(RS)-3-amino-1, 2-propanediol (50.0 mg, 0.094 mmol) to DMF (300.0 muL) and the solution was sonicated for 10 min to dissolve the material. MOF-520 single crystals (1.0 mg) impregnated with DMF were added to the solution. The vial was capped and placed in preheated 100 C. oven for 3 days. SXRD data was collected with a single crystal from the vial.

Molecular Weight:191.22
XLogP3:-0.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:191.11575802
Monoisotopic Mass:191.11575802
Topological Polar Surface Area:78.8
Heavy Atom Count:13
Complexity:164
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes