Water → HCID 17859365, compound

HRID 1372680Notes

Reaction equation

HRID 1372680 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][C:19]([O:21]C)=[O:20])=[C:13]([F:23])[CH:12]=1.[OH-].[Na+].O>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][C:19]([OH:21])=[O:20])=[C:13]([F:23])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 58778789HCID 58778789, compound

Product 1

HCID 17859365HCID 17859365, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (4-(2-benzothiazolyl)amino-5-chloro-2-fluorophenyl)acetate (613 mg, 1.68 mmol) was dissolved in THF (5 ml). To the resulting solution was added 1N NaOH (5.0 ml, 5.00 mmol). The resulting mixture was stirred at room temperature for 17 hours. Water was added to the reaction mixture. The mixture was washed with ether. The water layer was poured in ice-1N HCl to acidify the water layer. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (4-(2-benzothiazolyl)amino-5-chloro-2-fluorophenyl)acetic acid (464 mg, 82%) as a pale yellow solid.

Workup

  1. washThe mixture was washed with ether
  2. additionThe water layer was poured in ice-1N HCl
  3. customThe crystals thus precipitated
  4. filtrationwere collected by filtration under reduced pressure
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-82b7fe34655f415f8e44894ff313aff0
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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