Benzyl chloroformate → 1-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

HRID 415257Notes

Reaction equation

HRID 415257 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.C([O-])(O)=O.[Na+].[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1.O>[CH2:13]([O:20][C:21]([N:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 931923-azetidinecarboxylic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acidYield 102%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To the solution of azetidine-3-carboxylic acid (1 g, 10 mmol) of tetrahydrofuran/water (50 ml:50 ml) was added NaHCO3 (2.05 g, 25 mmol). Then benzyloxycarbonyl chloride (2.02 g, 12 mmol) was added dropwise at 0° C. The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and adjusted to pH=2, extracted with ethyl acetate. The residue was dried in vacuum. 2.4 g of crude 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid was obtained.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate
  3. customThe residue was dried in vacuum

Sources & evidence

ORD record
ord-4f591a9c53144b0ab762f22e27bb2ccc
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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