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-cyclohexyloxycarbonyloxy)-ethyl ester hydrochloride

HRID 1895666Notes

Reaction equation

HRID 1895666 reaction equation
[CH:1]1([O:7][C:8]([O:10][CH2:11][CH2:12][O:13][C:14]([C:16]2[N:17]=[C:18]([C:47]([F:50])([F:49])[F:48])[N:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:46])[CH2:26][C@H:27]([NH:38]C(OC(C)(C)C)=O)[CH2:28][C:29]4[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:30]=4[F:37])[CH2:21][C:20]=23)=[O:15])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:51]>C(OCC)(=O)C>[ClH:51].[CH:1]1([O:7][C:8]([O:10][CH2:11][CH2:12][O:13][C:14]([C:16]2[N:17]=[C:18]([C:47]([F:48])([F:49])[F:50])[N:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:46])[CH2:26][C@H:27]([NH2:38])[CH2:28][C:29]4[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:30]=4[F:37])[CH2:21][C:20]=23)=[O:15])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86646926(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-cyclohexyloxycarbonyloxy)-ethyl ester

Product 1

HCID 86646927(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-cyclohexyloxycarbonyloxy)-ethyl ester hydrochlorideYield 96.1%

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-cyclohexyloxycarbonyloxy)-ethyl ester 38a (0.25 g, 0.347 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 added to the flask under stirring. The reaction mixture was stirred at room temperature overnight 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-cyclohexyloxycarbonyloxy)-ethyl ester hydrochloride 38 (0.22 g, yield 96.1%) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e1ad4709eb06434ea589c0711920d567
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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