Sodium Hydroxide → HCID 67408351, compound

HRID 1372615Notes

Reaction equation

HRID 1372615 reaction equation
[OH-].[Na+:2].[F:3][C@@H:4]1[CH2:8][N:7]([C:9](=[O:28])[CH2:10][C:11]2[CH:27]=[CH:26][C:14]3[N:15]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])[O:17][C:13]=3[CH:12]=2)[C@H:6]([CH2:29][O:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[CH2:5]1>C(O)C>[F:3][C@@H:4]1[CH2:8][N:7]([C:9](=[O:28])[CH2:10][C:11]2[CH:27]=[CH:26][C:14]3[N:15]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])[O:17][C:13]=3[CH:12]=2)[C@H:6]([CH2:29][O:30][CH2:31][CH2:32][CH2:33][C:34]([O-:36])=[O:35])[CH2:5]1.[Na+:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44571247HCID 44571247, compound

Product 1

HCID 67408351HCID 67408351, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy-n-butyrate (378 mg, 0.782 mmol) was dissolved in THF (20 ml). To the resulting solution was added 0.25N NaOH (20 ml) and the mixture was stirred at 50° C. for 18 hours. The reaction mixture was concentrated under reduced pressure. 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 then purified by thin-layer silica gel column chromatography (TLC), whereby from chloroform/methanol (10/1) eluate fractions, 4-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy)-n-butyric acid (99 mg, 27%) was obtained as a yellow oil. Ethanol (3 ml) and 1N NaOH (211 μl, 0.211 mmol) were added to the resulting 4-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy)-n-butyric acid (99 mg, 0.211 mmol) under stirring to dissolve the latter in the former. The resulting solution was concentrated to dryness. Ether was added to crystallize the residue, whereby sodium 4-((2S,4S)-4-fluoro-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy)-n-butyrate (81 mg) was obtained as a solid.

Workup

  1. dissolutionto dissolve the latter in the former
  2. concentrationThe resulting solution was concentrated to dryness
  3. additionEther was added
  4. customto crystallize the residue

Sources & evidence

ORD record
ord-188494e4e08f4ff48a240cf95c8650f2
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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