N,S-Diacetyl-DL-cysteinyl-L-proline tert-butyl ester → N,S-diacetyl-DL-cysteinyl-L-proline

HRID 1447993Notes

Reaction equation

HRID 1447993 reaction equation
C([O:5][C:6](=[O:24])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:23])[CH:13]([CH2:18][S:19][C:20](=[O:22])[CH3:21])[NH:14][C:15](=[O:17])[CH3:16])(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[C:15]([NH:14][CH:13]([C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:24])=[O:5])=[O:23])[CH2:18][S:19][C:20](=[O:22])[CH3:21])(=[O:17])[CH3:16]

Participants

4

Reactant 1

HCID 14181603N,S-Diacetyl-DL-cysteinyl-L-proline tert-butyl ester

Product 1

HCID 12774422N,S-diacetyl-DL-cysteinyl-L-proline

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

N,S-Diacetyl-DL-cysteinyl-L-proline tert-butyl ester (1.9 g) is dissolved in a mixture of anisole (6 ml) and trifluoroacetic acid (12 ml) and the solution is stored at room temperature for one hour. The solvents are removed in vacuo and the residue is precipitated from ethyl acetate-ether-hexane, to obtain N,S-diacetyl-DL-cysteinyl-L-proline, yield 1.08 g, m.p. 80°-140°.

Workup

  1. customThe solvents are removed in vacuo
  2. customthe residue is precipitated from ethyl acetate-ether-hexane

Sources & evidence

ORD record
ord-3125060d5c494f7db449137983ac982d
Source dataset
uspto-grants-1979_12
Patent number
US04179434

Reaction notes

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