Ethanol → HCID 67406656, compound

HRID 1372628Notes

Reaction equation

HRID 1372628 reaction equation
[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:26])[CH2:8][C:9]2[CH:25]=[CH:24][C:12]3[N:13]=[C:14]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:23])[O:15][C:11]=3[CH:10]=2)[C@H:4]([CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36]C)=[O:35])[CH2:3]1.[OH-].[Na+:39].C(O)C.CCOCC>C1COCC1>[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:26])[CH2:8][C:9]2[CH:25]=[CH:24][C:12]3[N:13]=[C:14]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[CH3:23])[O:15][C:11]=3[CH:10]=2)[C@H:4]([CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O-:36])=[O:35])[CH2:3]1.[Na+:39]

Participants

6

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 14798Sodium Hydroxide2×HCID 58778621HCID 58778621, compound

Product 1

HCID 67406656HCID 67406656, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy)hexanoate (330 mg, 0.645 mmol) was dissolved in THF (30 ml). At room temperature, 0.25N NaOH (30 ml) was added and the mixture was stirred for 24 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 thin-layer silica gel chromatography, followed by separation by using chloroform/methanol (20/1), whereby the title compound (238 mg, 74%) was obtained as a yellow oil. Ethanol (10 ml) and 1N NaOH (0.478 ml, 0.478 mmol) were added to the resulting carboxylic acid derivative (238 mg, 0.478 mmol). After stirring for 10 minutes, ether was added to crystallize the residue, which had been obtained by distilling off the solvent under reduced pressure, whereby sodium 6-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy)hexanoate (199 mg) was obtained.

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 thin-layer silica gel chromatography
  9. customfollowed by separation
  10. customwas obtained as a yellow oil
  11. stirringAfter stirring for 10 minutes
  12. customto crystallize the residue, which
  13. customhad been obtained
  14. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-c347ae6a0afa4e5798f2552e292eebb4
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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