1-Methyl-L-tryptophan

The 10.2g tryptophan added 130mL of dimethyl sulfoxide (DMSO), under nitrogen protective stripUnder parts, within 30min, the batch was added5g of sodium hydroxide, After the addition of sodium hydroxide was stirred at room temperature for an hour, With an ice temperature of the system is then reduced to 0 , the iodide 7.46g 30mLDMSOTryptophan was added dropwise, DMSO solution of sodium amide in 30min, the subsequent addition was completeContinued reaction was stirred 15h, tryptophan complete the reaction, the system was added 50mL of water, the reaction was quenched, The reaction mixture was poured into 400mL of ether, there are large amount of solid precipitated, suction filtered, the resulting solidDissolved in water to obtain a solution, concentrated hydrochloric acid was added between the pH adjusted to 6-7, the precipitated solid was suction filtered out, The product was dried to give 8.7 g of white powder (yield 80percent, m.p.269 ).Same as in Example 1, the product was subjected to 1H-NMR and 13C-NMR nuclear magneticVibration, infrared and mass spectral analyzes. The results (not shown) indicated that the solid product obtained was 1-methylTryptophan, a purity of 100percent.Example - 59 Preparation of (R, S) l-[2-amino-3- (l-methyl-lH-indol-3-yl) -propionyl]-pyrrolidine-2- carbonitrile, compound with trifluoro-acetic acid Stage-l Preparation of (R) 2-tert~Butoxycarbonylamino-3- (l-methyl-lH-indol-3-yl) -propionic acid L-Tryptophan (0.5g, 2.0mmol) was weighed and charged in to 100 mL round bottom flask, to this sodium hydroxide solution (0.18g, 4.5mmol) in 1OmL of water and 1 mL dioxane was charged, stirring started cooling applied, to this clear solution Boc anhydride was charged, cooling removed, ambient temperature was maintained for 2-3 h. reaction was monitored by TLC, after completion of the reaction, reaction mixture was diluted with water and then cooled, acidified with 10percent Hydrochloric acid till the pH=l, and then extracted with ethyl acetate (2x100 mL) both the ethyl acetate layers were mixed washed with brine solution than dried over sodium sulphate and concentrated up to drynessgot the expected product Yield ( 0.65g, 95percent) . MS m/z 319(M + H+) .1H NMR (CDCl3, 300MHz) : deltal.4 (s, 9H) , 2.9 (dd, IH) , 3.1 (dd, IH) , 3.8 (s, 3H) , 4.1 (m, IH) , 7.0 (t, 2H) , 7.2 (t, 2H) , 7.4 (d, IH) , 7.6 (d, IH) , 12.6 (s, H)1-Methyl-L-tryptophan (1-Me-W; Aldrich Cat. No. 447439) is dissolved in the minimum amount of water and carefully treated with one equivalent of IN sodium hydroxide (NaOH) solution. Then 1.5 equivalents of FMOC chloride (Aldrich Cat. No. 23185) and 1.5 equivalents of IN NaOH are added alternately with stirring and cooling (ice-bath) under Schotten-Baumann conditions. After addition of both reagents is complete, the reaction mixture is stirred and allowed to warm slowly to room temperature for one hour. The reaction mixture is carefully acidified to pH about 2 with IN hydrochloric acid (HC1) to yield an off- white solid. This material is collected by vacuum filtration and dried in a vacuum dessicator to yield the desired product, N-FMOC-l-methyl-L-tryptophan. The material is stored at - 20°C until needed.

Molecular Weight:218.25
XLogP3:-1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:218.105527694
Monoisotopic Mass:218.105527694
Topological Polar Surface Area:68.2
Heavy Atom Count:16
Complexity:270
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes