Sodium Hydroxide → HCID 46912470, compound

HRID 1896099Notes

Reaction equation

HRID 1896099 reaction equation
[NH2:1][C@H:2]([CH2:22][C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=1[F:31])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]2[C:12]([C:18]([F:21])([F:20])[F:19])=[N:13][C:14]([C:15]([OH:17])=[O:16])=[C:8]2[CH2:7]1)=[O:5].[OH-].[Na+:33]>CO>[NH2:1][C@H:2]([CH2:22][C:23]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=1[F:31])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]2[C:12]([C:18]([F:21])([F:19])[F:20])=[N:13][C:14]([C:15]([O-:17])=[O:16])=[C:8]2[CH2:7]1)=[O:5].[Na+:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44194039HCID 44194039, compound

Product 1

HCID 46912470HCID 46912470, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(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 (100 mg, 0.22 mmol) was dissolved in 5 mL of methanol followed by addition of aqueous sodium hydroxide (0.44 mL, 0.22 mmol). The reaction was stirred for 15 minutes. The reaction mixture was concentrated under reduced pressure to obtain the title compound sodium (R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylate 4 (104 mg, 99.7%) as a white solid. HPLC: 99.65%. MS m/z (ESI): 451.2 [M+1]. 1H NMR (400 MHz, CD3OD, ppm): δ 7.26-7.30 (m, 1H), 7.08-7.13 (m, 1H), 5.00-5.20 (m, 2H), 4.26-4.27 (m, 2H), 4.00-4.11 (m, 2H), 3.44-3.48 (m, 1H), 2.72-2.83 (m, 2H), 2.59-2.60 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4625ea688b3d4b6394367ef8bf4724be
Source dataset
uspto-grants-2013_08
Patent number
US08518946B2

Reaction notes

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