Sodium Hydroxide → HCID 21071342, compound

HRID 1372592Notes

Reaction equation

HRID 1372592 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]3[CH2:25][C@@H:24]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][C@H:22]3[CH2:33][O:34][C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41]C)=[O:40])=[CH:37][CH:36]=3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]3[CH2:25][C@@H:24]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][C@H:22]3[CH2:33][O:34][C:35]3[CH:36]=[CH:37][C:38]([C:39]([OH:41])=[O:40])=[CH:43][CH:44]=3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778392HCID 58778392, compound

Product 1

HCID 21071342HCID 21071342, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-((2S,4S)-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-phenoxy-2-pyrrolidinylmethoxy)benzoate (640 mg, 1.07 mmol) in THF (30 ml) was added 0.25N NaOH (30 ml). The resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was then concentrated under reduced pressure. After addition of 1N HCl to the residue, the crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure, whereby the title compound (366 mg, 60%) was obtained as a pale pink solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionAfter addition of 1N HCl to the residue
  3. customthe crystals thus precipitated
  4. filtrationwere collected by filtration under reduced pressure
  5. washwashed with water
  6. dry with materialdried under reduced pressure, whereby the title compound (366 mg, 60%)
  7. customwas obtained as a pale pink solid

Sources & evidence

ORD record
ord-36ff6df1031a41e28fe09677f4b91bbc
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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