Methanol → HCID 59559322, compound

HRID 2075179Notes

Reaction equation

HRID 2075179 reaction equation
S(=O)(=O)(O)O.[CH:6]([N:19]1[CH2:22][C:21]([OH:26])([C:23]([OH:25])=[O:24])[CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:27]O>CCOC(C)=O>[CH:6]([N:19]1[CH2:20][C:21]([OH:26])([C:23]([O:25][CH3:27])=[O:24])[CH2:22]1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 203431191-Benzhydryl-3-hydroxy-azetidine-3-carboxylic acid

Product 1

HCID 59559322HCID 59559322, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Sulfuric acid (4.00 mL, 47.3 mmol) was added to a mixture of 1-benzhydryl-3-hydroxyazetidine-3-carboxylic acid (2.13 g, 7.50 mmol) in MeOH (20 mL). The mixture was heated to 80° C. for 18 h, diluted with EtOAc, extracted with water, 1N NaOH, dried over MgSO4, and evaporated. The solid was rinsed with Et2O to give methyl 1-benzhydryl-3-hydroxyazetidine-3-carboxylate. 1H NMR (300 MHz, CDCl3) δ ppm 7.43-7.49 (m, 4H), 7.24-7.31 (m, 4H), 7.15-7.23 (m, 2H), 4.54 (s, 1H), 3.90 (s, 3H), 3.59-3.72 (m, 2H), 3.24-3.39 (m, 2H). MS (ESI) m/z: Calculated; 297.14 Observed: 298.1 (M++1).

Workup

  1. extractionextracted with water, 1N NaOH
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. washThe solid was rinsed with Et2O

Sources & evidence

ORD record
ord-ce37410891a343e5bafd5ce204a63255
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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