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 isopropyl ester hydrochloride

HRID 221499Notes

Reaction equation

HRID 221499 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([C:38]([F:41])([F:40])[F:39])[N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:37])[CH2:17][C@H:18]([NH:29]C(OC(C)(C)C)=O)[CH2:19][C:20]3[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=3[F:28])[CH2:12][C:11]=12)=[O:6])([CH3:3])[CH3:2].[ClH:42]>C(OCC)(=O)C>[ClH:42].[CH:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([C:38]([F:40])([F:39])[F:41])[N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:37])[CH2:17][C@H:18]([NH2:29])[CH2:19][C:20]3[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=3[F:28])[CH2:12][C:11]=12)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59548961(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 isopropyl ester

Product 1

HCID 44194523(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 isopropyl ester hydrochlorideYield 97.8%

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 isopropyl ester 35a (0.17 g, 0.29 mmol) and 10 mL of ethyl acetate were added into the reaction flask. A solution of 5.5 N hydrochloric acid in 5 mL of ethyl acetate was then added to the reaction flask in an ice-water bath. Upon completion of the addition, the ice-water bath was removed. 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, and washed with n-hexane (10 mL×2). 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 isopropyl ester hydrochloride 35 (0.15 g, yield 97.8%) 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 n-hexane (10 mL×2)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d54a7fc23cc14a9eb3e19765d0fc3790
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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