Sodium Hydroxide → HCID 21087357, compound

HRID 348446Notes

Reaction equation

HRID 348446 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][S:5][C:6]1[N:11]=[CH:10][C:9]([C:12](=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:8][N:7]=1.[OH-].[Na+]>C1COCC1.CO.O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:12]([C:9]2[CH:8]=[N:7][C:6]([S:5][CH2:4][C:3]([OH:22])=[O:2])=[N:11][CH:10]=2)=[O:21])=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 16004801HCID 16004801, compound

Product 1

HCID 21087357HCID 21087357, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid methyl ester (95.5 mg, 0.3 mmol) in THF (2 mL) and methanol (0.25 mL) was added 1 N NaOH (0.3 mL). After 20 min an additional 0.2 mL of 1 N NaOH was added, and after 40 min an additional 0.1 mL 1 N NaOH was added. After 45 min total reaction time the solution was diluted with water and extracted with ethyl acetate. The organic layers were combined and washed once with water. The aqueous layers were combined and acidified to pH 1 with 3% HCl resulting in the formation of a solid precipitate. The solids were collected by filtration, washed and dried to afford 79.9 mg (88% yield) of the titled acid as a pale beige solid. API-MS m/z 308 (MH+), 306 (M−H)−.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed once with water
  3. filtrationThe solids were collected by filtration
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-e86904493e8d46428d7c915ef516ca12
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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