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Anthranilamide → 4-[1-(2-Carbamoylphenylcarbamoyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 238236
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HRID 238236 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]([OH:18])=O)[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([NH2:24])=[O:23].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCN(CC)CC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([C:16](=[O:18])[NH:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22](=[O:23])[NH2:24])[CH3:15])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
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참가 물질

7

반응물 4

HCID 6942AnthranilamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 177818912-[1-(Tert-butoxycarbonyl)piperidin-4-yl]propanoic acid

생성물 1

HCID 599933244-[1-(2-Carbamoylphenylcarbamoyl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester수율 53.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회
HCID 8471Triethylamine용매

실험 절차

A mixture of 4-(1-carboxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (28.6 g, 0.11 mol), 2-aminobenzamide (13.7 g, 0.1 mol), EDCI (21.3 g, 0.11 mol), HOBT (15 g, 0.11 mol) and Et3N (25 mL) in CH2Cl2 (500 mL) was stirred for 48 hr. The reaction mixture was diluted with CH2Cl2 (1000 mL) and washed with NaHCO3 (aq), the organic layer was dried with Na2SO4 and concentrated in vacuo to give the product a yellow solid (20 g, 48%) which was used directly for the next step.

후처리

  1. washwashed with NaHCO3 (aq)
  2. dry with materialthe organic layer was dried with Na2SO4
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4605a8e3df2948349118e090ad701c52
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642609B2

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