Hydrochloric Acid → (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

HRID 1895588Notes

Reaction equation

HRID 1895588 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C:36]([F:39])([F:38])[F:37])[N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:35])[CH2:15][C@H:16]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17][C:18]3[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=3[F:26])[CH2:10][C:9]=12)=[O:4].[OH-].[Na+].Cl>CO>[C:31]([O:30][C:28]([NH:27][C@H:16]([CH2:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=1[F:26])[CH2:15][C:14]([N:11]1[CH2:12][CH2:13][N:8]2[C:7]([C:36]([F:38])([F:39])[F:37])=[N:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]2[CH2:10]1)=[O:35])=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59548953(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 methyl ester

Product 1

HCID 59548952(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 acidYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 methyl ester 1n (2.0 g, 3.5 mmol) was dissolved in 50 mL of methanol under stirring, and 4 N sodium hydroxide solution (30 mL) was added to the solution. The reaction mixture was reacted at room temperature for an hour until thin lay chromatography showed the starting material disappeared, and was adjusted to pH 3 with a 2 N hydrochloric acid solution. The reaction mixture was extracted with ethyl acetate (50 mL×4), and the combined organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (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 2a (1.9 g) as a light yellow solid.

Workup

  1. customThe reaction mixture was reacted at room temperature for an hour
  2. extractionThe reaction mixture was extracted with ethyl acetate (50 mL×4)
  3. dry with materialthe combined organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a3cbff24dc084d028bc6e319e5c163ee
Source dataset
uspto-grants-2013_08
Patent number
US08513411B2

Reaction notes

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