Hydrochloric Acid → HCID 44194429, compound

HRID 1895656Notes

Reaction equation

HRID 1895656 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[N:12]=[C:13]([C:42]([F:45])([F:44])[F:43])[N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:41])[CH2:21][C@H:22]([NH:33]C(OC(C)(C)C)=O)[CH2:23][C:24]3[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=3[F:32])[CH2:16][C:15]=12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:46]>C(OCC)(=O)C>[ClH:46].[CH2:1]([O:8][C:9]([C:11]1[N:12]=[C:13]([C:42]([F:44])([F:45])[F:43])[N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:41])[CH2:21][C@H:22]([NH2:33])[CH2:23][C:24]3[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=3[F:32])[CH2:16][C:15]=12)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59548958HCID 59548958, compound

Product 1

HCID 44194429HCID 44194429, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 benzyl ester 33a (0.056 g, 0.087 mmol) and a solution of 2.7 N hydrochloric acid in 2 mL of ethyl acetate were added into the reaction flask. The reaction mixture was stirred at room temperature for 2 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure 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 benzyl ester hydrochloride 33 (0.043 g, yield 86%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-77710d3d35f447c992bb4165d5bb2d94
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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