Hydrochloric Acid → HCID 74018218, compound

HRID 1819510Notes

Reaction equation

HRID 1819510 reaction equation
C1COCC1.[OH-].[Na+].C([O:10][C:11](=[O:46])[C:12]([CH3:45])=[CH:13][C:14]1[C:19]([F:20])=[CH:18][C:17]([C:21](=[O:43])[NH:22][C:23]2[S:24][CH:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]([O:40][CH3:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:29]=3[F:42])[N:27]=2)=[CH:16][C:15]=1[F:44])C.Cl>CO>[F:44][C:15]1[CH:16]=[C:17]([C:21](=[O:43])[NH:22][C:23]2[S:24][CH:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]([O:40][CH3:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:29]=3[F:42])[N:27]=2)[CH:18]=[C:19]([F:20])[C:14]=1[CH:13]=[C:12]([CH3:45])[C:11]([OH:46])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 74018211HCID 74018211, compound

Product 1

HCID 74018218HCID 74018218, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of THF (2 mL), methanol (2 mL), and 2N sodium hydroxide aqueous solution of 3-(2,6-difluoro-4-{4-[2-fluoro-3-(1-methyloxyhexyl)phenyl]thiazol-2-ylcarbamoyl}phenyl}-2-methylacrylic acid ethyl ester (500 mg) was stirred at room temperature for 3 h. The reaction mixture was acidified with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and brine, dried over magnesium sulfate, and evaporated. The residue was recrystallized from ethyl acetate to obtain the compoumd (B1) 370 mg.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f108e92a43c04b47af7423e62fcdcdeb
Source dataset
uspto-grants-2009_10
Patent number
US07601746B2

Reaction notes

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