Sodium Hydroxide → HCID 178525890, compound

HRID 1423930Notes

Reaction equation

HRID 1423930 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][NH:6][C:7]([C:9]1[C:10](=[O:21])[S:11][C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][CH:15]=[C:14]([F:20])[CH:13]=2)=[O:8])C.[OH-].[Na+]>O1CCCC1.CO>[F:20][C:14]1[CH:13]=[C:12]2[C:17]([C:18]([OH:19])=[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:22])=[O:3])=[O:8])[C:10](=[O:21])[S:11]2)=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178472763HCID 178472763, compound

Product 1

HCID 178525890HCID 178525890, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

[(7-Fluoro-4-hydroxy-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid ethyl ester (150 mg, 0.461 mmol) was dissolved in a mixture of tetrahydrofuran (5 mL) and methanol (5 mL). 1N Sodium hydroxide (1.85 mL) was added to the solution and the reaction was stirred overnight (18 h) at ambient temperature. The reaction was concentrated in vacuo and the residue dissolved in water, treated with 1N HCl to pH 3 to precipitate the product, which was collected via filtration and dried to yield [(7-fluoro-4-hydroxy-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid (100 mg, 75%.) MS ESI(−) m/e: 296.23 (M−1).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue dissolved in water
  3. additiontreated with 1N HCl to pH 3
  4. customto precipitate the product, which
  5. filtrationwas collected via filtration
  6. customdried

Sources & evidence

ORD record
ord-0c198ee0c146452fb90e52d50880fa8b
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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