Lithium Hydroxide → HCID 71257850, compound

HRID 1183176Notes

Reaction equation

HRID 1183176 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][C@H:6]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[N:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])[N:18]=1)=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])C.[OH-].[Li+]>C1COCC1.O>[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][O:22][C:20]1[N:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])[N:18]=[C:17]([C:15]([NH:14][C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[CH2:5][C:4]([OH:39])=[O:3])=[O:16])[CH:21]=1)#[N:31]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67361465HCID 67361465, compound

Product 1

HCID 71257850HCID 71257850, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

210 mg (0.4 mmol) of (S)-3-{[5-(2-cyano-benzyloxy)-1-(2-fluoro-phenyl)-1H-pyrazole-3-carbonyl]-amino}-3-o-tolyl-propionic acid ethyl ester were dissolved in a mixture of THF, MOH and water (2 ml each), lithium hydroxide (28.7 mg, 1.2 mmol) was added, and the mixture was stirred for 3 h at room temperature. After evaporation of the solvent the residue was subjected to aqueous work-up using EA and a 10% aqueous solution of citric acid. After evaporation of the organic phase the residue was subjected to column chromatography (silica gel, DCM/MOH 10:1) to give 45 mg (23%) of the title compound.

Workup

  1. additionwas added
  2. customAfter evaporation of the solvent the residue
  3. customAfter evaporation of the organic phase the residue

Sources & evidence

ORD record
ord-c84ee7c7c9bd48debe12c4b7ab6ab346
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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