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

HRID 894855Notes

Reaction equation

HRID 894855 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-02fe133fe1994dc4a00e733dd577404e
Source dataset
uspto-grants-1981_08
Patent number
US04284780

Reaction notes

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