Potassium Hydroxide → HCID 46912472, compound

HRID 1896101Notes

Reaction equation

HRID 1896101 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-].[K+: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].[K+:33]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 44194039HCID 44194039, compound

Product 1

HCID 46912472HCID 46912472, compoundYield 100.5%

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 potassium 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 potassium (R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylate 6 (108 mg, 100%) as a white solid. HPLC: 92.78%. MS m/z (ESI): 451.2 [M+1]. 1H NMR (400 MHz, CD3OD, ppm): δ 7.31-7.38 (m, 1H), 7.14-7.23 (m, 1H), 5.07-5.27 (m, 2H), 4.26-4.36 (m, 2H), 4.01-4.15 (m, 2H), 3.52-3.60 (m, 1H), 2.80-2.92 (m, 2H), 2.59-2.74 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4d86258ce0c8490d831b109e2b6705b2
Source dataset
uspto-grants-2013_08
Patent number
US08518946B2

Reaction notes

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