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

HRID 1252818Notes

Reaction equation

HRID 1252818 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-D,L-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-D,L-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-884b6ea940f74f0fb932a035c4af6d03
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

Loading…