Sodium Hydroxide → 4-((2S,4S)-1-(7-Fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-fluoro-2-pyrrolidinylmethoxy)benzoic acid

HRID 1372576Notes

Reaction equation

HRID 1372576 reaction equation
[F:1][C:2]1[C:10]2[O:9][C:8]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([N:22]1[CH2:26][C@@H:25]([F:27])[CH2:24][C@H:23]1[CH2:28][O:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[CH:32][CH:31]=1)=[O:21].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[C:10]2[O:9][C:8]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([N:22]1[CH2:26][C@@H:25]([F:27])[CH2:24][C@H:23]1[CH2:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:38][CH:39]=1)=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778812Methyl 4-((2S,4S)-1-(7-fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-fluoro-2-pyrrolidinylmethoxy)benzoate

Product 1

HCID 587786284-((2S,4S)-1-(7-Fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-fluoro-2-pyrrolidinylmethoxy)benzoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-((2S,4S)-1-(7-fluoro-2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-fluoro-2-pyrrolidinylmethoxy)benzoate (490 mg, 0.915 mmol) was dissolved in THF (40 ml). To the resulting solution was added 0.25N NaOH (40 ml), followed by stirring at room temperature for 14 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was acidified with 1N HCl, followed by extraction with a chloroform/methanol (10/1) mixture. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/methanol (20/1) eluate fractions, the title compound (394 mg, 83%) was obtained as a colorless amorphous substance.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. extractionfollowed by extraction with a chloroform/methanol (10/1) mixture
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/methanol (20/1) eluate fractions

Sources & evidence

ORD record
ord-f8b7663c60644894864453c0656c7adc
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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