Sulfuric Acid → 1-Benzhydryl-3-hydroxy-azetidine-3-carboxylic acid

HRID 2075178Notes

Reaction equation

HRID 2075178 reaction equation
[CH:1]([N:14]1[CH2:17]C(O[Si](C)(C)C)(C#N)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:26].[O:30]1[CH2:35][CH2:34][O:33]CC1>>[CH:1]([N:14]1[CH2:15][C:34]([OH:33])([C:35]([OH:30])=[O:26])[CH2:17]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 579892141-(Diphenylmethyl)-3-[(trimethylsilyl)oxy]azetidine-3-carbonitrile

Product 1

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

Conditions

Temperature
95 °C

Procedure

1-Benzhydryl-3-(trimethylsilyloxy)azetidine-3-carbonitrile (2.85 g, 8.47 mmol) was taken up in a 1:1 mixture of 1,4-dioxane (30 mL) and 60% aqueous sulfuric acid (30 mL). The mixture was heated to 95° C. for 1 h. The solvent was removed and the residue was taken to pH 7 using 5N NaOH. The solid was isolated by filtration, rinsed with Et2O to give 1-benzhydryl-3-hydroxyazetidine-3-carboxylic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.36-7.47 (m, 4H), 7.22-7.33 (m, 4H), 7.13-7.23 (m, 2H), 4.52 (s, 1H), 3.46 (d, J=8.3 Hz, 2H), 3.02 (d, J=8.2 Hz, 2H). MS (ESI) m/z: Calculated; 283.1 Observed: 284.1 (M++1).

Workup

  1. customThe solvent was removed
  2. customThe solid was isolated by filtration
  3. washrinsed with Et2O

Sources & evidence

ORD record
ord-e58140023f93499f8518acecf46d25d9
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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