Dimethylformamide → HCID 86745958, 화합물

HRID 893851

반응식

HRID 893851 반응식
CN(C)[CH:3]=[O:4].[CH2:6]([O:8][C:9]([CH:11]1[CH:19]2[C:14]3([CH:23]=[CH:22][CH:21]=[CH:20][C:15]3=[N:16][CH2:17][CH2:18]2)[S:13][CH2:12]1)=[O:10])[CH3:7].[CH3:24][O:25][C:26]1[CH:42]=[CH:41][C:29]([CH2:30][O:31][C:32]([NH:34][CH:35]([CH2:39][CH3:40])C(O)=O)=[O:33])=[CH:28][CH:27]=1.P(C#N)(OCC)(OCC)=[O:44]>C(OCC)(=O)C.C(N(CC)CC)C>[CH2:6]([O:8][C:9]([CH:11]1[CH:19]2[C:14]3([CH:23]=[CH:22][CH:21]=[CH:20][C:15]3=[N:16][CH2:17][CH2:18]2)[S:13][CH:12]1[C:3](=[O:4])[CH2:40][CH2:39][CH2:35][NH:34][C:32]([O:31][C:30](=[O:44])[C:29]1[CH:28]=[CH:27][C:26]([O:25][CH3:24])=[CH:42][CH:41]=1)=[O:33])=[O:10])[CH3:7]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 76257Diethyl cyanophosphonateHCID 19891224HCID 19891224, 화합물HCID 199609281,2,3,4-Tetrahydro-benzo[b]thieno[2,3,c]pyridine-3-carboxylic acid ethyl ester

생성물 1

HCID 86745958HCID 86745958, 화합물

시약·촉매·용매 2

HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

2-(4-Aminobutyroyl)-1,2,3,4-tetrahydro-benzo[b]thieno[2,3-c]pyridine-3-carboxylic acid ethyl ester was obtained by the following method. To 5 ml of dimethylformamide were added 392 mg of 1,2,3,4-tetrahydro-benzo[b]thieno[2,3-c]pyridine-3-carboxylic acid ethyl ester and 441 mg of p-methoxybenzyloxycarbonylaminobutyric acid and after further adding thereto 269 mg of diethyl cyanophosphate and 251 of triethylamine, the mixture was stirred for 2 hours at 50° C. After finishing the reaction, 100 ml of ethyl acetate was added to the reaction mixture and the mixture was washed thrice with 100 ml of water. The ethyl acetate layer was concentrated under reduced pressure and subjected to silica gel column chromatography (development solvent: chloroform and methanol of 50:1) to provide 2-[4-(p-methoxybenzoyl)oxycarbonylaminobutyroyl]-1,2,3,4-tetrahydro-benzo[b]thieno[2,3-c]pyridine-3-carboxylic acid ethyl ester. Then, 5 ml of a mixture of 1N hydrochloric acid and ethyl acetate was added to the product and the mixture was stirred for one hour at 50° C. and then cooled to provide 315 mg (yield of 54%) of 2-(4-aminobutyroyl)-1,2,3,4-tetrahydro-benzo[b]thieno[2,3-c]pyridine-3-carboxylic acid ethyl ester.hydrochloride.

후처리

  1. additionafter further adding
  2. additionwas added to the reaction mixture
  3. washthe mixture was washed thrice with 100 ml of water
  4. concentrationThe ethyl acetate layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6f11446b00714fd58938c444719191de
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05126448

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