1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-Acetoxybenzamide

HRID 908545

반응식

HRID 908545 반응식
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])(=[O:3])[CH3:2].[NH2:14]CC1SC=CC=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([NH2:14])=[O:9])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 34005(2-Thienylmethyl)amineHCID 757711-HydroxybenzotriazoleHCID 2386693-Acetoxybenzoic acid

생성물 1

HCID 2761253-Acetoxybenzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-acetoxybenzoic acid (8.1 mg, 0.0450 mmol), 5-aminomethylthiophene 18d (22.3 mg, 0.0473 mmol), 1-hydroxybenzotriazole (HOBt, 4.7 mg, 0.0348 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDC, 8.5 mg, 0.0443 mmol) was dissolved in DMF (0.6 ml) and stirred overnight at r.t. Work-up (AcOEt/H2O; brine/Na2SO4), concentration, filtration over a silica gel plug (EtOAc) and evaporation gave the intermediate 3-acetoxybenzamide, which was deacetylated by siring in MeOH (2 ml) and Et3N (0.4 ml) for 1 h at 55° C. Evaporation gave 28.5 mg (103%) of the title 3-hydroxy-benzamide as a colorless oil.

후처리

  1. concentration(AcOEt/H2O; brine/Na2SO4), concentration, filtration
  2. customover a silica gel plug (EtOAc) and evaporation

출처 및 근거

ORD 기록
ord-62074c12e1934f7584e7a72101ba98fb
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017628B2

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