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 tert-butyl ester hydrochloride

HRID 1895662Notes

Reaction equation

HRID 1895662 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:39]([F:42])([F:41])[F:40])[N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:38])[CH2:18][C@H:19]([NH:30]C(OC(C)(C)C)=O)[CH2:20][C:21]3[CH:26]=[C:25]([F:27])[C:24]([F:28])=[CH:23][C:22]=3[F:29])[CH2:13][C:12]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:43]>C(OCC)(=O)C>[ClH:43].[C:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:39]([F:40])([F:41])[F:42])[N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:38])[CH2:18][C@H:19]([NH2:30])[CH2:20][C:21]3[CH:26]=[C:25]([F:27])[C:24]([F:28])=[CH:23][C:22]=3[F:29])[CH2:13][C:12]=12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59548966HCID 59548966, compound

Product 1

HCID 44194525(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 tert-butyl ester hydrochlorideYield 100%

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 tert-butyl ester 36a (0.094 g, 0.15 mmol) and 10 mL of ethyl acetate were added into the reaction flask. A solution of 5.5 N hydrochloric acid in 3 mL of ethyl acetate was added to the reaction flask in a ice-water bath. Upon completion of the addition, the ice-water bath was removed. The reaction mixture was stirred at room temperature for 3 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure, and washed with 20 mL of n-hexane. The filtrate 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 tert-butyl ester hydrochloride 36 (0.084 g, yield 100%) as a white solid.

Workup

  1. additionUpon completion of the addition
  2. customthe ice-water bath was removed
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washwashed with 20 mL of n-hexane
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a42be4b4fd0461d9f79ca3fac6e5b91
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

Loading…