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

HRID 1372585
Notes
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Reaction equation

HRID 1372585 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:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH:28]=4)[CH2:23][C@H:22]3[CH2:37][O:38][C:39]3[CH:48]=[CH:47][C:42]([C:43]([O:45]C)=[O:44])=[CH:41][CH:40]=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:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH:28]=4)[CH2:23][C@H:22]3[CH2:37][O:38][C:39]3[CH:48]=[CH:47][C:42]([C:43]([OH:45])=[O:44])=[CH:41][CH:40]=3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778786methyl 4-((2S,4S)-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-(2-naphthyloxy)-2-pyrrolidinylmethoxy)benzoate

Product 1

HCID 587783864-((2S,4S)-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-(2-naphthyloxy)-2-pyrrolidinylmethoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-((2S,4S)-1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-4-(2-naphthyloxy)-2-pyrrolidinylmethoxy)benzoate (312 mg, 0.486 mmol) in THF (20 ml) was added 0.25N NaOH (20 ml). The resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was then concentrated under reduced pressure. The residue was acidified with 1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure, whereby the title compound (253 mg, 83%) was obtained as a pale pink solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe crystals thus precipitated
  3. filtrationwere collected by filtration under reduced pressure
  4. washwashed with water
  5. dry with materialdried under reduced pressure, whereby the title compound (253 mg, 83%)
  6. customwas obtained as a pale pink solid

Sources & evidence

ORD record
ord-27cdc3e5599948f988cf6d7bdef71915
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07157487B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes