S-benzyl-(L)-cysteine methyl ester → N-[(S,S)-2,4-dibenzyl-4-carboxy-butyryl]-S-benzyl-(L)-cysteine methyl ester

HRID 1493449Notes

Reaction equation

HRID 1493449 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:6][S:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:5].[CH2:16]([C@@H:23]1[CH2:29][C@@H:28]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27](=[O:37])[O:26][C:24]1=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:6][S:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH:5][C:27](=[O:37])[C@H:28]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:29][C@@H:23]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:24]([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 450313S-benzyl-(L)-cysteine methyl esterHCID 14557658(S,S)-2,4-dibenzylglutaric anhydride

Product 1

HCID 14997155N-[(S,S)-2,4-dibenzyl-4-carboxy-butyryl]-S-benzyl-(L)-cysteine methyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4.5 g of S-benzyl-(L)-cysteine methyl ester and 2.8 g of (S,S)-2,4-dibenzylglutaric anhydride in 25 ml of pyridine and 25 ml of methylene chloride is stirred at room temperature overnight. The mixture is concentrated, the residue is dissolved in ether and the solution is washed with lN hydrochloric acid, saturated sodium chloride, dried over magnesium sulfate, concentrated, to yield N-[(S,S)-2,4-dibenzyl-4-carboxybutyryl]-S-benzyl-(L)-cysteine methyl ester (oil).

Workup

  1. concentrationThe mixture is concentrated
  2. dissolutionthe residue is dissolved in ether
  3. washthe solution is washed with lN hydrochloric acid, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2394bc07364640e9942710a865a3112e
Source dataset
uspto-grants-1991_06
Patent number
US05021430

Reaction notes

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