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

HRID 374323Notes

Reaction equation

HRID 374323 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 1N hydrochloric acid, saturated sodium chloride, dried over magnesium sulfate, concentrated, to yield N-[(S,S)-2,4-dibenzyl-4-carboxy-butyryl]-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 1N hydrochloric acid, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e0b82574981f4bfba0f4b99d1007a451
Source dataset
uspto-grants-1992_11
Patent number
US05166212

Reaction notes

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