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2,6-Lutidine → Methyl 4-[6-(cyclopentyloxycarbonyl)aminobenzimidazol-1-ylmethyl]-3-methoxybenzoate

HRID 1646350
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HRID 1646350 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH2:10][C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=3[O:21][CH3:22])[C:6]=2[CH:23]=1.N1C(C)=CC=CC=1C.Cl[C:33]([O:35][CH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:34]>ClCCl>[CH:36]1([O:35][C:33]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[N:9]=[CH:8][N:7]([CH2:10][C:11]4[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=4[O:21][CH3:22])[C:6]=3[CH:23]=2)=[O:34])[CH2:40][CH2:39][CH2:38][CH2:37]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 2735892Cyclopentyl chloroformateHCID 14763098Methyl 4-(6-aminobenzimidazol-1-ylmethyl)-3-methoxybenzoate

생성물 1

HCID 14763099Methyl 4-[6-(cyclopentyloxycarbonyl)aminobenzimidazol-1-ylmethyl]-3-methoxybenzoate수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of methyl 4-(6-aminobenzimidazol-1-ylmethyl)-3-methoxybenzoate (J) (0.63 g.) and 2,6lutidine (0.36 ml.) in dichloromethane (10 ml.) was treated with cyclopentyl chloroformate (0.33 g.). After stirring for 24 hours the solution was diluted with dichloromethane. The mixture was washed successively with 20% w/v sodium hydroxide, water, and brine, then dried (MgSO4) and evaporated. The resultant residue was purified by flash chromatography on a 6×20 cm. silica gel column using 1:3 v/v hexane:ethyl acetate as the eluent to give the title compound (0.57 g., 93%): NMR: 1.7 [m,8 H, (CH2)4 ], 3.8 (s,3 H, OCH3), 3.9 (s,3 H, OCH3) 5.2 (m,1 H, CHO), 6.17-7.0 (br m,3 H), 7.5-7.8 (br m,4 H).

후처리

  1. washThe mixture was washed successively with 20% w/v sodium hydroxide, water, and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe resultant residue was purified by flash chromatography on a 6×20 cm

출처 및 근거

ORD 기록
ord-75c57051c3b04bc096a6f1d1abded498
출처 데이터셋
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05179112

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