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

HRID 1976550Notes

Reaction equation

HRID 1976550 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>N1CCNCC1.O>[CH2:24]([O:23][C:21]([N:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 931923-azetidinecarboxylic Acid

Product 1

HCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 4837PiperazineCatalystHCID 962WaterSolvent

Procedure

To azetidine-3-carboxylic acid (0.50 g), potassium carbonate (0.82 g), dioxan (5 mL), water (10 mL) was added benzyl chloroformate (0.74 mL) at room temperature for 6 h under nitrogen. Piperazine (5 drops) was then added. After ½ h, the dioxan was removed in vacuo and the residue diluted with 2M hydrochloric acid (25 mL). After extracting with ethyl acetate (35 mL), the organic layer was washed with brine (10 mL) and dried (MgSO4). Solvent removal in vacuo gave Intermediate 13 as a colourless oil (1.07 g).

Workup

  1. customthe dioxan was removed in vacuo
  2. additionthe residue diluted with 2M hydrochloric acid (25 mL)
  3. extractionAfter extracting with ethyl acetate (35 mL)
  4. washthe organic layer was washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent removal in vacuo

Sources & evidence

ORD record
ord-f0585cb576424675a5d5932e5c7bdbe9
Source dataset
uspto-grants-2001_05
Patent number
US06228853B1

Reaction notes

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