Water → HCID 86649986, compound

HRID 1892478Notes

Reaction equation

HRID 1892478 reaction equation
[Br-].[C:2]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:7][C:6]=1[F:31])([OH:4])=[O:3].[CH:32]([C:34]1[N:35]=[C:36]([NH:39][C:40](=[O:42])[CH3:41])[S:37][CH:38]=1)=O.CC(C)([O-])C.[K+].O>CN(C)C=O>[C:40]([NH:39][C:36]1[S:37][CH:38]=[C:34]([CH:32]=[CH:9][C:8]2[CH:29]=[CH:30][C:5]([C:2]([OH:4])=[O:3])=[C:6]([F:31])[CH:7]=2)[N:35]=1)(=[O:42])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 14931749N-(4-Formyl-1,3-thiazol-2-YL)acetamideHCID 23665647Potassium tert-butoxideHCID 86649984HCID 86649984, compound

Product 1

HCID 86649986HCID 86649986, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-carboxy-3-fluorobenzyl)(triphenyl)phosphoniumbromide (2.037 g, 4.112 mmol) and N-(4-formyl-1,3-thiazol-2-yl)acetamide (599.5 mg, 3.523 mmol) in anhydrous N,N-dimethylformamide (15 ml) was added potassium tert-butoxide (1.180 g, 10.52 mmol), and the mixture was stirred at room temperature for 3 hr. Water (150 ml) was added to the reaction mixture, and the mixture was washed 3 times with ethyl acetate. While stirring, 1M hydrochloric acid (10.5 ml) was added to the aqueous layer. The precipitated solid was collected by filtration and washed with water. The solid was dried under reduced pressure to give 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]vinyl}-2-fluorobenzoic acid (753.9 mg, 2.461 mmol, yield 69.9%) as a yellow solid.

Workup

  1. washthe mixture was washed 3 times with ethyl acetate
  2. stirringWhile stirring
  3. addition1M hydrochloric acid (10.5 ml) was added to the aqueous layer
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-73fdae5453e740be96aee81903f292c2
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

Loading…