反应 #543565

ord-3f77f430f45d456ca00d6aea223a2153

反应方程式

CC[O-].[Na+]
sodium ethylate
O=C(O)CCCBr
4-bromobutyric acid
O=C(n1ccnc1)n1ccnc1
1,1′-carbonyldiimidazol
CC(=O)N[C@@H](CS)C(=O)O
N-acetyl cysteine
CC(=O)N[C@@H](CSC(=O)CCCBr)C(=O)O
N-acetyl-S-(4-bromobutyroyl) cysteine

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.STIRRINGunder stirring
  2. 2
    洗涤After 24 hours the solution is washed with HCl 1% and brine
  3. 3
    其他evaporated at reduced pressure
  4. 4
    其他The obtained crude product
  5. 5
    其他is purified by chromatography on silica gel column
  6. 6
    洗涤eluting with ethyl acetate/chloroform 7/3

实验过程

A solution of 4-bromobutyric acid (5.1 g, 30.6 mmoles) and 1,1′-carbonyldiimidazol (5.61 g, 34.6 mmoles)) in chloroform (50 ml) is left at room temperature under stirring for 1 hour. To the reaction mixture N-acetyl cysteine (5 g, 30.6 mmoles) dissolved in N,N-dimethylformamide (5 ml) and sodium ethylate (50 mg) is added under stirring. After 24 hours the solution is washed with HCl 1% and brine, the organic phase is anhydrified with sodium sulphate and evaporated at reduced pressure. The obtained crude product is purified by chromatography on silica gel column, eluting with ethyl acetate/chloroform 7/3. N-acetyl-S-(4-bromobutyroyl) cysteine is obtained.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07186708B2uspto-grants-2007_03