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 221503Notes

Reaction equation

HRID 221503 reaction equation
[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]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59548960HCID 59548960, compound

Product 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 hydrochlorideYield 91.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(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.

Workup

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

Sources & evidence

ORD record
ord-94ab91dd77bd4ded80a72edf65ef3099
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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