Calcium Hydroxide → HCID 86663125, compound

HRID 1896102Notes

Reaction equation

HRID 1896102 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-].[Ca+2:33].[OH-]>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].[Ca+2:33].[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]

Participants

4

Reactant 2

HCID 6093208Calcium HydroxideHCID 44194039HCID 44194039, compound

Product 1

HCID 86663125HCID 86663125, compoundYield 100%

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 10 mL of methanol followed by addition of aqueous calcium hydroxide solution (8.1 mg, 0.11 mmol). The mixture was stirred for 20 hours. The reaction mixture was concentrated under reduced pressure to obtain the title compound calcium (R)-7-[3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylate 7 (103 mg, 100%) as a white solid. HPLC: 99.60%. MS m/z (ESI): 451.2 [M+1]. 1H NMR (400 MHz, CD3OD, ppm): δ 7.28-7.34 (m, 1H), 7.11-7.21 (m, 1H), 5.10-5.21 (m, 2H), 4.22-4.36 (m, 2H), 4.03-4.09 (m, 2H), 3.55-3.59 (m, 1H), 2.76-2.85 (m, 2H), 2.60-2.71 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3f8a5b934e6d4defb2b6e28edcaf60cf
Source dataset
uspto-grants-2013_08
Patent number
US08518946B2

Reaction notes

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