n,s-dibenzoylcysteine → HCID 56624824, compound

HRID 615682Notes

Reaction equation

HRID 615682 reaction equation
[C:1]([NH:9][CH:10]([C:21]([OH:23])=O)[CH2:11][S:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([NH:28][C@H:29]([C:40]([OH:42])=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)(C)(C)C>>[C:1]([NH:9][C@H:10]([C:21]([NH:28][C@H:29]([C:40]([OH:42])=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=[O:23])[CH2:11][S:12][C:13](=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 230089n,s-dibenzoylcysteineHCID 54122649HCID 54122649, compound

Product 1

HCID 56624824HCID 56624824, compound

Procedure

N-(N,S-Dibenzoyl-D,L-cysteinyl)-tryptophan was obtained as a diastereomer mixture (melting point 175°-178° C., petroleum ether; Rf=0.19 and 0.16 in system II) by a procedure similar to that described in Example 16, using N,S-dibenzoyl-D,L-cysteine and tert.-butyl tryptophan as starting materials. Recrystallization from diethyl ether gave N-(N,S-dibenzoylcysteinyl)-tryptophan (melting point 210°-213° C., Rf=0.19 in system II) in a form which was pure according to thin-layer chromatography. N-(N,S-dibenzoyl-D-cysteinyl)-tryptophan (melting point 157°-160° C., Rf=0.16 in system II) which was pure according to thin-layer chromatography was obtained from the mother liquor after crystallization from petroleum ether.

Workup

  1. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-c6570a7b77834bdeaf7323d2ca910276
Source dataset
uspto-grants-1985_02
Patent number
US04500467

Reaction notes

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