Sodium Hydroxide → HCID 24958677, compound

HRID 1430620Notes

Reaction equation

HRID 1430620 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:26])[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])([CH3:16])[CH2:14][CH3:15])[S:9][CH:10]=1)C.[OH-].[Na+]>CO.O>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[O:17][C:13]([CH3:16])([CH2:14][CH3:15])[C:12]([NH:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:27])=[O:3])[N:7]=1)=[O:26]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59363853HCID 59363853, compound

Product 1

HCID 24958677HCID 24958677, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of {2-[2-(2,4-Difluoro-phenoxy)-2-methyl-butyrylamino]-thiazol-4-yl}-acetic acid ethyl ester (0.202 g, 0.51 mmol) in MeOH (3 ml) and water (1.5 ml). NaOH (0.041 g, 1.1 mmol) was added and stirred at room temperature for 16 hrs. The organic solvent was evaporated and residue was diluted with water (2 ml) and acidified (pH˜2) with 5% HCl. The aqueous layer was extracted with ethyl acetate (2×10 ml) and organic layer was washed with saturated brine (10 ml). The organic layer was dried over Na2SO4 and evaporated under reduced pressure to obtain crude product which was solidified by triturating with hexane to afford {2-[2-(2,4-Difluoro-phenoxy)-2-methyl-butyrylamino]-thiazol-4-yl}-acetic acid (0.158 g, 84%). 1H NMR (400 MHz, CDCl3): δ1.03 (t, J=7.6 Hz, 3H), 1.44 (s, 3H), 1.86-1.9 (m, 1H), 2.05-2.09 (m, 1H), 3.78 (s, 2H), 6.78 (s, 1H), 6.80-6.84 (m, 1H), 6.88-6.93 (m, 1H), 7.0-7.06 (m, 1H), 10.6 (s, 1H), MS (EI) m/z: 371.00 (M+1) and mp: 148-149° C.

Workup

  1. customThe organic solvent was evaporated
  2. additionresidue was diluted with water (2 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×10 ml) and organic layer
  4. washwas washed with saturated brine (10 ml)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated under reduced pressure
  7. customto obtain crude product which
  8. customby triturating with hexane

Sources & evidence

ORD record
ord-1bdd60f7e90e4a5fbe8159d2d38ffafc
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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