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 1895664Notes

Reaction equation

HRID 1895664 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-b7f55dd7a2b54f80a744b7d4b0673aff
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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