Sodium Hydroxide → 1-Benzhydryl-3-hydroxy-azetidine-3-carboxylic acid

HRID 1672898Notes

Reaction equation

HRID 1672898 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]2[CH2:11][C:10]([OH:15])([C:12](N)=[O:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:22].[Na+]>C(O)C.O>[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]2[CH2:11][C:10]([OH:15])([C:12]([OH:22])=[O:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 596518481-(Diphenylmethyl)-3-hydroxyazetidine-3-carboxamide

Product 1

HCID 203431191-Benzhydryl-3-hydroxy-azetidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(Diphenylmethyl)-3-hydroxyazetidine-3-carboxamide (1.1 g, 3.90 mmol) was treated with 10% sodium hydroxide in ethanol (15 mL) and water (2 mL) at reflux for 2 h and then was concentrated in vacuo. The residue was neutralized with 1 N hydrochloric acid (pH ˜7) and the precipitate was collected by filtration and lyophilized to afford 1-(diphenylmethyl)-3-hydroxyazetidine-3-carboxylic acid (assume 3.90 mmol) which was used without further purification: 1H NMR (400 MHz, d6-DMSO): 7.45-7.40 (m, 4H), 7.31-7.25 (m, 4H), 7.21-7.15 (m, 2H), 4.52 (s, 1H), 3.46 (dd, 2H), 3.02 (dd, 2H); MS (EI) for C17H17NO3: 284 (MH+).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationwas concentrated in vacuo
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5c5d49dc202245df8e068d993515fd13
Source dataset
uspto-grants-2011_08
Patent number
US07999006B2

Reaction notes

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