Sodium Chloride → N-acetyl-DL-cysteinyl-L-proline

HRID 1762517Notes

Reaction equation

HRID 1762517 reaction equation
[C:1]([NH:4][CH:5]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])[CH2:6][S:7]C(=O)C)(=[O:3])[CH3:2].[Cl-].[Na+]>O.N>[C:1]([NH:4][CH:5]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])[CH2:6][SH:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 12774422N,S-diacetyl-DL-cysteinyl-L-proline

Product 1

HCID 14181605N-acetyl-DL-cysteinyl-L-proline

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

N,S-Diacetyl-D,L-cysteiny--L-proline (0.3 g.) is dissolved in a mixture of water (4 ml.) and concentrated ammonia (4 ml.) under a blanket of argon. The solution is stored for thirty minutes at room temperature, saturated with sodium chloride and extracted with ethyl acetate and chloroform. The organic layers are pooled and concentrated to dryness in vacuo to obtain N-acetyl-D,L-cysteinyl-L-proline, yield 0.1 g., Rf =0.25 (silica gel; benzene:acetic acid, 75:25).

Workup

  1. extractionextracted with ethyl acetate and chloroform
  2. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-da3883fd6ffd42749d44edbc47614a20
Source dataset
uspto-grants-1989_05
Patent number
US04833152

Reaction notes

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