Salicylic Acid → Tert-butyl 2-(2-hydroxybenzamido)propylcarbamate

HRID 919142노트

반응식

HRID 919142 반응식
[NH2:1][CH:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[OH:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].N1C=CN=C1.C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[OH:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH:1][CH:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:17]

참가 물질

6

반응물 4

HCID 338Salicylic AcidHCID 795ImidazoleHCID 10868DicyclohexylcarbodiimideHCID 22499135tert-Butyl (2-aminopropyl)carbamate

생성물 1

HCID 67493246Tert-butyl 2-(2-hydroxybenzamido)propylcarbamate수율 40%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of tert-butyl 2-aminopropylcarbamate (3.6 g, 20.6 mmol), 2-hydroxybenzoic acid (2.79 g, 20.6 mmol) and imidazole (1.41 g, 20.6 mmol) in EtOAc (100 mL) at 0° C. was slowly added a solution of DCC (4.26 g, 20.6 mmol) in EtOAc (50 mL). The reaction mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography, EtOAc/Petroleum ether (0-20%) to afford tert-butyl 2-(2-hydroxybenzamido)propylcarbamate (2.4 g, 40%) as a white solid.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by silica chromatography, EtOAc/Petroleum ether (0-20%)

출처 및 근거

ORD 기록
ord-4afec4944d52472d93fe904201321fa3
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09272984B2

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