Sodium Hydroxide → 1279038-40-2

HRID 1183174Notes

Reaction equation

HRID 1183174 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]([NH:19][C@H:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[CH2:21][C:22]([O:24]CC)=[O:23])=[O:18])=[N:11]1>CC1CCCO1>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]([NH:19][C@H:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[CH2:21][C:22]([OH:24])=[O:23])=[O:18])=[N:11]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67361977HCID 67361977, compound

Product 1

HCID 533087431279038-40-2Yield 82%

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

82.8 ml of an aqueous 4 M solution of sodium hydroxide (331 mmol) were added to a solution of ethyl (S)-3-{[1-(2-fluoro-phenyl)-5-methoxy-1H-pyrazole-3-carbonyl]-amino}-3-(2-methyl-phenyl)-propionate (70.4 g, 165 mmol) in 2-methyltetrahydrofuran (500 ml) at room temperature. The mixture was stirred at room temperature for 2 h, then at 40° C. for 2 h and then at room temperature for 16 h. The phases were separated and the aqueous phase acidified to pH 3 with hydrochloric acid. The product partially precipitated upon acidification. The aqueous filtrate was extracted with EA. The extracts were evaporated and the residue was washed with isopropyl acetate. The two batches were combined to give 53.6 g (82%) of the title compound as a white crystalline powder.

Workup

  1. waitat 40° C. for 2 h
  2. waitat room temperature for 16 h
  3. customThe phases were separated
  4. customThe product partially precipitated upon acidification
  5. extractionThe aqueous filtrate was extracted with EA
  6. customThe extracts were evaporated
  7. washthe residue was washed with isopropyl acetate

Sources & evidence

ORD record
ord-d8a041e59c25482987610ec211ed4bb8
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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