Lithium Hydroxide → HCID 46912471, compound

HRID 1896100Notes

Reaction equation

HRID 1896100 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-].[Li+: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].[Li+:33]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 44194039HCID 44194039, compound

Product 1

HCID 46912471HCID 46912471, compoundYield 98.6%

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 lithium hydroxide solution (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 lithium (R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylate 5 (48 mg, 98.6%) as a white solid. HPLC: 99.66%. MS m/z (ESI): 451.2 [M+1]. 1H NMR (400 MHz, CD3OD, ppm): δ 7.31-7.38 (m, 1H), 7.13-7.22 (m, 1H), 5.07-5.27 (m, 2H), 4.26-4.36 (m, 2H), 4.01-4.15 (m, 2H), 3.53-3.60 (m, 1H), 2.80-2.91 (m, 2H), 2.59-2.72 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f32194868ba0482da19d99b4ac4a9f86
Source dataset
uspto-grants-2013_08
Patent number
US08518946B2

Reaction notes

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