反应 #1340619

ord-35d54dbb7afb491192dffff2fa80e251

反应方程式

Nc1ccc(C(=O)O)cc1
4-aminobenzoic acid
O=C(Cl)C1CCCCC1
cyclohexanecarbonyl chloride
CCN(CC)CC
Et3N
[Na+].[OH-]
NaOH
COC(=O)c1ccc(NC(=O)C2CCCCC2)cc1
methyl 4-(cyclohexanecarboxamido)benzoate
O=C(O)c1ccc(NC(=O)C2CCCCC2)cc1
48d
收率 92.0%
O=C(O)c1ccc(NC(=O)C2CCCCC2)cc1
4-(Cyclohexanecarboxamido)benzoic acid
收率 92.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.STIRRINGthe reaction mixture was stirred for 5 h at room temperature
  2. 2
    其他The THF was removed by rotary evaporation and 1N aqueous HCl
  3. 3
    workup.ADDITIONwas added
  4. 4
    其他to precipitate the product, which
  5. 5
    过滤was filtered

实验过程

A mixture of 4-aminobenzoic acid 48a (1.98 mmol, 300 mg), cyclohexanecarbonyl chloride 48b (1.98 mmol, 291 mg), and Et3N (2.52 mmol, 0.43 mL) in 6 mL of THF was stirred at room temperature overnight. 1N aqueous NaOH (7.9 mmol, 7.9 mL) was added to the mixture (containing methyl 4-(cyclohexanecarboxamido)benzoate 48c) and the reaction mixture was stirred for 5 h at room temperature. The THF was removed by rotary evaporation and 1N aqueous HCl was added to precipitate the product, which was filtered to give 480 mg (92%) of 48d.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08455476B2uspto-grants-2013_06