Benzoyl chloride → N-benzoyl-gamma-L-glutamyl-taurine

HRID 2285688Notes

Reaction equation

[NH2:1][C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][CH2:4][C:5]([NH:7][CH2:8][CH2:9][S:10]([OH:13])(=[O:12])=[O:11])=[O:6].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:17]([NH:1][C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][CH2:4][C:5]([NH:7][CH2:8][CH2:9][S:10]([OH:13])(=[O:12])=[O:11])=[O:6])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 687595-L-glutamyl-taurine

Product 1

HCID 86738334N-benzoyl-gamma-L-glutamyl-taurine

Procedure

25.4 mg. (0.1 mmoles) of gamma-L-glutamyl-taurine are treated with 13 μl. of benzoyl chloride as described in Example 12. The reaction mixture is processed as described in Example 12 to obtain N-benzoyl-gamma-L-glutamyl-taurine, which is purified by paper electrophoresis using a pH 6.5 buffer solution. Relative motility (related to cysteinic acid): 1.06. Rf =0.47 (in a 15:10:3:12 mixture of n-butanol, pyridine, glacial acetic acid and water).

Sources & evidence

ORD record: ord-1f37613aaa5542eabbe6bb93cb622c2b
Source dataset: uspto-grants-1982_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04324743

Reaction notes

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