Oxalyl chloride → Benzyl 3-(chlorocarbonyl)azetidine-1-carboxylate

HRID 245685Notes

Reaction equation

HRID 245685 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]([OH:17])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:21])=O>ClCCl.CN(C)C=O>[Cl:21][C:15]([CH:13]1[CH2:14][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12]1)=[O:17]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

Product 1

HCID 86674648Benzyl 3-(chlorocarbonyl)azetidine-1-carboxylateYield 102.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid (21.25 mmol, 5 g) in dichloromethane (60 ml) under a nitrogen atmosphere were added N,N-dimethylformamide (1.063 mmol, 0.083 ml) and oxalyl chloride (2M solution in dichloromethane, 25.00 mmol, 12.5 ml). After stirring at room temperature for two hours the reaction mixture was concentrated in vacuo to give 5.53 gram of crude benzyl 3-(chlorocarbonyl)azetidine-1-carboxylate.

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-2168f576f3204af9ab23bec4b2d50b4c
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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