Hydrochloric Acid → 7-[3-Amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 1-isopropoxycarbonyloxy-ethyl ester hydrochloride

HRID 221503노트

반응식

HRID 221503 반응식
[CH:1]([O:4][C:5]([O:7][CH:8]([O:10][C:11]([C:13]1[N:14]=[C:15]([C:44]([F:47])([F:46])[F:45])[N:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:43])[CH2:23][C@H:24]([NH:35]C(OC(C)(C)C)=O)[CH2:25][C:26]3[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:27]=3[F:34])[CH2:18][C:17]=12)=[O:12])[CH3:9])=[O:6])([CH3:3])[CH3:2].[ClH:48]>C(OCC)(=O)C>[ClH:48].[CH:1]([O:4][C:5]([O:7][CH:8]([O:10][C:11]([C:13]1[N:14]=[C:15]([C:44]([F:45])([F:46])[F:47])[N:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:43])[CH2:23][C@H:24]([NH2:35])[CH2:25][C:26]3[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:27]=3[F:34])[CH2:18][C:17]=12)=[O:12])[CH3:9])=[O:6])([CH3:2])[CH3:3].[ClH:48].[CH:1]([O:4][C:5]([O:7][CH:8]([O:10][C:11]([C:13]1[N:14]=[C:15]([C:44]([F:45])([F:46])[F:47])[N:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:43])[CH2:23][CH:24]([NH2:35])[CH2:25][C:26]3[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:27]=3[F:34])[CH2:18][C:17]=12)=[O:12])[CH3:9])=[O:6])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 59548960(R)-7-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 1-isopropoxycarbonyloxy-ethyl ester

생성물 2

HCID 44194527(R)-7-[3-Amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 1-isopropoxycarbonyloxy-ethyl ester hydrochlorideHCID 749472057-[3-Amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 1-isopropoxycarbonyloxy-ethyl ester hydrochloride수율 91.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

(R)-7-[3-tert-Butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 1-isopropoxycarbonyloxy-ethyl ester 37a (0.29 g, 0.43 mmol) and 5 mL of ethyl acetate were added into the reaction flask. A solution of 6.5 N hydrochloric acid in 3 mL of ethyl acetate was then added to the flask. The reaction mixture was stirred at room temperature for 4 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound R)-7-[3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 1-isopropoxycarbonyloxy-ethyl ester hydrochloride 37 (0.24 g, yield 91.2%) as a white solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-94ab91dd77bd4ded80a72edf65ef3099
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207161B2

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