Chloroform → HCID 57190921, compound

HRID 1733655Notes

Reaction equation

HRID 1733655 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22]([OH:24])=O)[CH2:13][S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH2:31])[CH3:27].C(Cl)(Cl)Cl.CS(ON1C2C=CC=CC=2N=N1)(=O)=O>C(OCC)(=O)C.O.C(N(CC)CC)C>[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH:31][C:22](=[O:24])[C@H:12]([CH2:13][S:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:27]

Participants

8

Reactant 4

HCID 6212ChloroformHCID 98775N-[(Phenylmethoxy)carbonyl]-S-(phenylmethyl)-L-cysteineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 57190921HCID 57190921, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxycarbonyl-S-benzyl-L-cysteine (1.73 g) and glycine ethyl ester hydrochloride (0.70 g) are suspended into chloroform (20 ml) and therein is dissolved triethylamine (1.4 ml). To the solution is added 1-methanesulfonyloxy-1,2,3-benzotriazole (1.07 g) with stirring under ice-cooling. The mixture is stirred for 2 hours and then allowed to stand overnight. To the reaction mixture are added water and ethyl acetate. The ethyl acetate layer is separated and washed with water, 1 N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate and water in order and then dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off and the resulting residue is crystallized from petroleum ether to give N-(N-benzyloxycarbonyl-S-benzyl-L-cysteinyl)glycine ethyl ester (1.25 g), melting pont: 89°-93° C. The product is identified with an authentic sample by infrared spectrum.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred for 2 hours
  3. customThe ethyl acetate layer is separated
  4. washwashed with water, 1 N hydrochloric acid
  5. dry with materiala saturated aqueous sodium hydrogen carbonate and water in order and then dried over anhydrous magnesium sulfate
  6. customAfter drying
  7. distillationthe solvent is distilled off
  8. customthe resulting residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-7782070c44144ae29add4b8b6cefe5b4
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

Loading…