Sodium Hydroxide → HCID 58778986, compound

HRID 1372578Notes

Reaction equation

HRID 1372578 reaction equation
C([O:4][C@@H:5]1[CH2:9][N:8]([C:10](=[O:29])[CH2:11][C:12]2[CH:28]=[CH:27][C:15]3[N:16]=[C:17]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:26])[O:18][C:14]=3[CH:13]=2)[C@H:7]([CH2:30][O:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38]C)=[O:37])=[CH:34][CH:33]=2)[CH2:6]1)(=O)C.[OH-].[Na+]>C1COCC1>[OH:4][C@@H:5]1[CH2:9][N:8]([C:10](=[O:29])[CH2:11][C:12]2[CH:28]=[CH:27][C:15]3[N:16]=[C:17]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:26])[O:18][C:14]=3[CH:13]=2)[C@H:7]([CH2:30][O:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778667HCID 58778667, compound

Product 1

HCID 58778986HCID 58778986, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-((2S,4S)-4-acetoxy-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-2-pyrrolidinylmethoxy)benzoate (610 mg, 1.09 mmol) in THF (40 ml) was added 0.25N NaOH (40 ml). The resulting mixture was stirred at room temperature 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 water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent, whereby the title compound (500 mg, 92%) was obtained as a pale pink amorphous substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionfollowed by extraction with a chloroform-methanol (10/1) mixture
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto remove the solvent, whereby the title compound (500 mg, 92%)
  7. customwas obtained as a pale pink amorphous substance

Sources & evidence

ORD record
ord-5b9c64ec30c94b4c884c6723aeff5e62
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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