Sodium Hydroxide → HCID 21463509, compound

HRID 1940627Notes

Reaction equation

HRID 1940627 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[S:11][C:12]2[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([F:21])[C:13]=2[N:14]=1.[OH-].[Na+]>O.O1CCOCC1>[F:21][C:15]1[C:13]2[N:14]=[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:22])=[O:2])[S:11][C:12]=2[C:18]([F:19])=[CH:17][C:16]=1[F:20]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 53715288HCID 53715288, compound

Product 1

HCID 21463509HCID 21463509, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7-(4,5,7-trifluorobenzothiazol-2-yl)heptanoic acid methyl ester (407 mg, 1.2 mmol) in a mixture of water (7 ml) and dioxane (7 ml) was added dropwise aqueous 2N sodium hydroxide (4 ml) at room temperature and the mixture was stirred for 5 hours at room temperature. To the mixture further aqueous 2N sodium hydroxide (2 ml) was added dropwise and the resulting mixture was stirred for 1 hour, then diluted with water and extracted with ethyl acetate. The aqueous phase was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried and then evaporated to yield a residue, which was crystallized from isopropyl ether to give 7-(4,5,7-trifluorobenzothiazol-2-yl)heptanoic acid (189 mg, 50%) as a colorless powder.

Workup

  1. stirringthe resulting mixture was stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. customto yield a residue, which
  8. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-50e432eee07841aaac31a556e86e4034
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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