Benzyl chloroformate → (2S)-1-(Benzyloxycarbonyl)azetidine-2-carboxylic acid

HRID 737165Notes

Reaction equation

HRID 737165 reaction equation
[NH:1]1[CH2:4][CH2:3][C@H:2]1[C:5]([OH:7])=[O:6].CCN(C(C)C)C(C)C.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>CN(C=O)C>[CH2:21]([O:20][C:18]([N:1]1[CH2:4][CH2:3][C@H:2]1[C:5]([OH:7])=[O:6])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 16486L-Azetidine-2-carboxylic acidHCID 81531Diisopropylethylamine

Product 1

HCID 12088656(2S)-1-(Benzyloxycarbonyl)azetidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(S)-Azetidine-2-carboxylic acid (250.4 mg, 2.5 mmol) was dissolved in DMF (15 mL) and distilled water (6 mL). The solution was cooled to 0° C., and DIEA (645 μL, 3.7 mmol) was added followed by benzyl chloroformate (530 μL, 3.7 mmol). The reaction was stirred at 0° C. and allowed to warm to ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product.

Workup

  1. distillationdistilled water (6 mL)
  2. temperatureto warm to ambient temperature overnight
  3. filtrationThe reaction was filtered
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-373f0e26a7b0400da0644ed4b6833ce9
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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