Citric Acid → HCID 9825123, compound

HRID 2298424Notes

Reaction equation

[Li+].[OH-].C([O:5][C:6]([C:8]1[N:9]=[C:10]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[N:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[N:14]=2)[CH:12]=1)=[O:7])C.CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C1COCC1>[C:22]1([C@@H:20]([NH:19][C:15]2[N:14]=[C:13]([N:11]3[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[N:9]=[C:10]3[C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=3)[CH:18]=[CH:17][N:16]=2)[CH3:21])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

LiOH (3.75 g, 0.1566 mol) dissolved in a minimum amount of water was added to (S)-1-[2-(1-phenylethylamino)pyrimidin-4-yl]-2-(3-trifluoromethylphenyl)-1H-imidazole-4-carboxylic acid ethyl ester (4.2 g, 0.0087 mol) in 20 mL THF. 3 mL MeOH was added and the solution warmed to 60° C. for 45 min. After cooling to room temperature, the reaction was acidified with pH 4.5 citric acid solution (buffered with NaOH) and extracted with ethyl acetate (2×150 mL). The ethyl acetate was dried over anhydrous magnesium sulfate and concentrated to give 3.5 g of a solid. The solid was stirred vigorously for 30 minutes as a slurry in Et2O and filtered to give the title compound (2.5 g ) as a solid.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate (2×150 mL)
dry with materialThe ethyl acetate was dried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-8ab78990d9dc43a19aba02e59ccd7fe8
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492516B1

Reaction notes

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