L-(+)-Cysteine → HCID 22846549, compound

HRID 2255037Notes

Reaction equation

HRID 2255037 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[C:10]1([CH2:16][C@H:17]([NH:28][C:29]([O:31]C(C)(C)C)=O)[CH2:18][NH:19][C@H:20]([C:25]([OH:27])=O)[C@H:21]([CH2:23][CH3:24])[CH3:22])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N[C@H:37](C(O)=O)[CH2:38][SH:39]>>[C:10]1([CH2:16][C@H:17]([NH:28][C:29](=[O:31])[CH2:37][CH2:38][SH:39])[CH2:18][NH:19][C@H:20]([C:25]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:27])[C@H:21]([CH2:23][CH3:24])[CH3:22])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 5862L-(+)-CysteineHCID 6137L-MethionineHCID 22846566HCID 22846566, compound

Product 1

HCID 22846549HCID 22846549, compound

Procedure

N-(3-phenyl-2(S)-(mercaptopropionylamino)prop-1-yl)isoleucyl-methionine was prepared by coupling resin-bound methionine to N-(3-phenyl-2(S)-t-butoxycarbonylaminopropyl)isoleucine followed by deprotection, coupling with a protected cysteine and further processing under standard solid phase synthesis conditions. FAB MS m/z 484 (M+1).

Sources & evidence

ORD record
ord-ecbbd6f4d3ba44b5be0c8ead858f616b
Source dataset
uspto-grants-1993_08
Patent number
US05238922

Reaction notes

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