L-(+)-Cysteine → N-(1-Oxotetradecyl)-L-cysteine

HRID 979257Notes

Reaction equation

HRID 979257 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[C:8](Cl)(=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[NH:1]([C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:22])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4]

Participants

3

Reactant 2

HCID 5862L-(+)-CysteineHCID 66986Myristoyl chloride

Product 1

HCID 21303830N-(1-Oxotetradecyl)-L-cysteine

Procedure

20 g (0.1652 mol) of Cys are reacted with 36.6 g (0.1487 mol) of myristoyl chloride analogously to Stage 6.1 to form tetradecanoyl-Cys: m.p.=63°-65°, Rf =0.13 (CH2Cl2 :acetone=8:2).

Sources & evidence

ORD record
ord-8a500c9e1a814fbbb35e013ef237a39b
Source dataset
uspto-grants-1987_05
Patent number
US04666886

Reaction notes

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