BENZYL N-(2-AMINOETHYL)CARBAMATE HYDROCHLORIDE

Under nitrogen protection, To 500 mLAdd three bottlesDichloromethane (100 mL), Ethylenediamine (39 mL, 0.58 mol)And potassium carbonate (32.4 g, 0.23 mol)The reaction temperature is controlled at -5 ~ 0 , A solution of benzyl chloroformate (20.0 g, 0.12 mol) in dichloromethane (100 mL) was slowly added dropwise with stirring. About 1h dripping is completed, Stir at room temperature for 2h.The reaction was washed with water (200 mL * 2)The organic layer was separated and the organic layer was dried over sodium sulfate (10 g)Concentrated under reduced pressure, Have a pale yellow foam 23.4g.Ethyl acetate (80 mL) was added to the residue, Stir at room temperature until completely dissolved, Slowly add petroleum ether (80 mL) dropwise, A white solid is generated(White solid benzyl formate), Filtration, the mother liquor was concentrated to give a pale yellow oil 15.1g, yield 66.5percent.Intermediate 9 Benzyl N-(2-aminoethyl) carbamate A solution of benzylchloroformate ( 1.3 mL, 9 mmol) in DCM (25 mL) was added over 1.5h to a solution of 1, 2-diaminoethane (6 mL, 90 mmol) in DCM (95 mL) cooled at 0°C. The solution was stirred for 2h at 0°C, then the solution was washed with brine (40 mL) . The organic phase was filtered through a phase separator and evaporated to dryness to obta in the title compound as a white solid ( 1.85 g) which was used in the next step without further purification. For liquid ethylenediamine (147mL, 2.2mol), was dissolved in 500mL dichloromethane. The ice bath was cooled to 0°C, benzyloxycarbonyl chloride dissolved in 1.5L of methylene chloride (30mL, 219mmol) was dissolved was slowly added dropwise to the reaction flask. System was returned to room temperature overnight. The reaction system was filtered, concentrated to remove part of the solvent, washing with water. Finally concentrated to give a pale yellow viscous liquid. After column chromatography to give a clear oily liquid (23g), i.e., compounds 9-3.Triphenylphosphine(6.7 g, 25.56 mmol) and water (15 mL) were added to asolution of compound 9 (3.8 g, 17.4 mmol) in MeOH(40 mL). The mixture was heated under reflux for 2 h. Themixture was concentrated under reduced pressure andpurified by column chromatography. The target productwas obtained as light brown oil (3 g, 90 percent). 1H NMR(CDCl3, 300 MHz) δ 7.33 (s, 5H), 5.73 (bs, 1H), 5.08 (s, 2H), 3.19 (bs, 2H), 2.76 (bs, 2H); 13C NMR (CDCl3, 75 MHz) δ 156.8, 136.6, 128.5, 128.0, 66.6, 43.6, 41.5;LC-MS: m/z calculated for C10H14N2O2: 194, Found :195(M+1) +.Preparation of N-(2-(4Z, 7Z, 10Z, 13Z, 16Z, 19Z)-docosa-4, 7, 10, 13, 16, 19-hexaenamidoethyl)-2-hydroxybenzamide (Ic-10); Ethylenediamine (1.0 g, 16.7 mmol) is dissolved in water (3.0 mL) containing bromoaresal green as an indicator. Methane sulfonic acid (2.8 g, 31 mmol) in water (3.0 ml) was added until a blue to pale yellow color transition is just achieved. The solution was diluted with ethanol (8.0 mL) and vigorously stirred. To the mixture was added the solution of Cbz-Cl (2.8 g, 16.7 mmol) in dimethoxyethane (4 mL) and 50percent w/v aqueous AcOK (10 mL) at 20° C. simultaneously to maintain the pale yellow-green color of the indicator. After the additions are complete the mixture was stirred (RT, 1 h) and concentrated at low temperature under vacuum to removed the volatiles. The residue was shaken with water (20 mL) and filtered. The filtrate was then washed with toluene (3.x.50 mL), basified with excess 40percent aqueous NaOH and extracted with toluene (3.x.50 mL). The organic layer was washed with brine (50 mL), dried over NaPreparation of benzyl (2-aminoethyl)carbamate To a solution of 2-(((benzyloxy)carbonyl)amino)ethanaminium chloride (1.0 g, 4.3 mmol) in water (5 mL) was added anhydrous NaStep 1 Step 1

Molecular Weight:194.23
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:194.105527694
Monoisotopic Mass:194.105527694
Topological Polar Surface Area:64.4
Heavy Atom Count:14
Complexity:168
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes