Hydrochloric Acid → (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-ethoxycarbonyloxy)-ethyl ester hydrochloride

HRID 221497Notes

Reaction equation

HRID 221497 reaction equation
[CH2:1]([O:3][C:4]([O:6][CH2:7][CH2:8][O:9][C:10]([C:12]1[N:13]=[C:14]([C:43]([F:46])([F:45])[F:44])[N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:42])[CH2:22][C@H:23]([NH:34]C(OC(C)(C)C)=O)[CH2:24][C:25]3[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=3[F:33])[CH2:17][C:16]=12)=[O:11])=[O:5])[CH3:2].[ClH:47]>C(OCC)(=O)C>[ClH:47].[CH2:1]([O:3][C:4]([O:6][CH2:7][CH2:8][O:9][C:10]([C:12]1[N:13]=[C:14]([C:43]([F:44])([F:45])[F:46])[N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:42])[CH2:22][C@H:23]([NH2:34])[CH2:24][C:25]3[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=3[F:33])[CH2:17][C:16]=12)=[O:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86646922(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-ethoxycarbonyloxy)-ethyl ester

Product 1

HCID 86646923(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-ethoxycarbonyloxy)-ethyl ester hydrochlorideYield 85%

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-ethoxycarbonyloxy)-ethyl ester 34a (0.26 g, 0.39 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 6 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-ethoxycarbonyloxy)-ethyl ester hydrochloride 34 (0.2 g, yield 85%) 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-52815ee926814c2a8b62cbd6469365da
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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