反应 #217562

ord-ea57d76ffdb64978a11f45d3a93ad583

反应方程式

O=C(O)CNC(=O)OCc1ccccc1
benzyloxycarbonyl glycine
CCN(C(C)C)C(C)C
diisopropylethylamine
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CC(=O)OCC=CCNCC#CC(=O)OC(C)(C)C
acetic acid 4-(tert-butoxy-carbonylprop-2-ynylamino)-but-2-enyl ester
CC(=O)OCC1C(N)CC2CN(C(=O)OC(C)(C)C)CC21
4-acetoxymethyl-5-aminooctahydrocyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester
CC(=O)OCC1C(NC(=O)CNC(=O)OCc2ccccc2)CC2CN(C(=O)OC(C)(C)C)CC21
title product
CC(=O)OCC1C(NC(=O)CNC(=O)OCc2ccccc2)CC2CN(C(=O)OC(C)(C)C)CC21
4-acetoxymethyl-5-(2-benzyloxycarbonylaminoacetylamino)octahydrocyclopenta[c]-pyrrole-2-carboxylic acid tert-butyl ester

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    浓缩The mixture is concentrated under vacuum
  2. 2
    其他yielding a residue
  3. 3
    其他The residue is purified by flash column chromatography

实验过程

By sequentially following the procedures of Example 3, Parts B and C, and Example 1, Parts A and B, acetic acid 4-(tert-butoxy-carbonylprop-2-ynylamino)-but-2-enyl ester is converted to 4-acetoxymethyl-5-aminooctahydrocyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester. A solution of this material and benzyloxycarbonyl glycine in acetonitrile is treated sequentially with diisopropylethylamine and TBTU, and the resulting mixture is stirred at room temperature until the reaction is complete. The mixture is concentrated under vacuum yielding a residue. The residue is purified by flash column chromatography providing the title product.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07381738B2uspto-grants-2008_06