Sodium Hydroxide → HCID 178525891, compound

HRID 1423952Notes

Reaction equation

HRID 1423952 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][NH:6][C:7]([C:9]1[C:10](=[O:27])[S:11][C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][C:15]([Cl:20])=[CH:14][C:13]=2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:8])C.[OH-].[Na+]>C1COCC1.CO>[Cl:20][C:15]1[CH:16]=[C:17]2[C:12](=[C:13]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:14]=1)[S:11][C:10](=[O:27])[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:28])=[O:3])=[O:8])=[C:18]2[OH:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178472765HCID 178472765, compound

Product 1

HCID 178525891HCID 178525891, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

[(6-Chloro-4-hydroxy-2-oxo-8-phenyl-2H-thiochromene-3-carbonyl)-amino]-acetic acid ethyl ester (200 mg, 0.479 mmol) was dissolved in THF-Methanol (1:1; 13 mL total volume.) Sodium hydroxide (1.5 mmol, 1.5 mL; 1M) was added and the solution stirred overnight at ambient temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in water (10 mL.) The crude product was precipitated with 1N HCl (3 mL) and isolated via filtration and triturated with hexanes to provide the title compound (177 mg.) MS ESI(+) m/e: 390.118, 392.226 (M+1).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in water (10 mL.) The crude product
  4. customwas precipitated with 1N HCl (3 mL)
  5. customisolated via filtration
  6. customtriturated with hexanes

Sources & evidence

ORD record
ord-a523c4c40aff4886adb0359c9913c660
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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