Sodium Hydroxide → HCID 44194039, compound

HRID 1896098Notes

Reaction equation

HRID 1896098 reaction equation
Cl.[NH2:2][C@H:3]([CH2:23][C:24]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=1[F:32])[CH2:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]2[C:13]([C:19]([F:22])([F:21])[F:20])=[N:14][C:15]([C:16]([OH:18])=[O:17])=[C:9]2[CH2:8]1)=[O:6].[OH-].[Na+]>CO>[NH2:2][C@H:3]([CH2:23][C:24]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=1[F:32])[CH2:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]2[C:13]([C:19]([F:22])([F:20])[F:21])=[N:14][C:15]([C:16]([OH:18])=[O:17])=[C:9]2[CH2:8]1)=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44194038HCID 44194038, compound

Product 1

HCID 44194039HCID 44194039, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-7-[3-Amino-4-(2,4,5-trifluoro-phenyl)-butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylic acid hydrochloride 1 (1.02 g, 2.1 mmol) was dissolved in 30 mL of methanol followed by addition of aqueous sodium hydroxide (2.1 mL, 2.1 mmol). The reaction was stirred for 15 minutes. The reaction mixture was concentrated under reduced pressure and the resulting solid was dissolved in 15 mL of the solvent mixture of dichloromethane/methanol (v:v=1:3). The mixture was filtered and concentrated under reduced pressure to obtain the title compound (R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 3 (943 mg, 100%) as a white solid. HPLC: 99.89%. MS m/z (ESI): 451.2 [M+1]. 1H NMR (400 MHz, CD3OD, ppm): δ 7.32-7.41 (m, 1H), 7.11-7.21 (m, 1H), 5.00-5.07 (m, 2H), 4.16-4.24 (m, 2H), 4.05-4.08 (m, 1H), 3.85-3.97 (m, 2H), 3.05-3.17 (m, 2H), 2.91-2.93 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting solid was dissolved in 15 mL of the solvent mixture of dichloromethane/methanol (v:v=1:3)
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0a5c22490354862b47f4029668741fb
Source dataset
uspto-grants-2013_08
Patent number
US08518946B2

Reaction notes

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