Dimethylformamide → (2S)-1-(Benzyloxycarbonyl)azetidine-2-carboxylic acid chloride

HRID 1264481Notes

Reaction equation

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

Participants

Conditions

Temperature: -5 °C

Procedure

(2S)-1-(benzyloxycarbonyl)azetidine-2-carboxylic acid (729.3 mg, 3.10 mmol, 1.0 eq) was dissolved in dry dichloromethane (15 mL) and cooled to about −5° C. under argon. Oxalyl chloride (380 μL, 4.36 mmol, 1.4 eq) and a drop of DMF were added to the solution. The mixture was warmed to reflux temperature with stirring over about a 3 hour period. After cooling, the mixture was concentrated and used in Reference Example 16.

Workup

temperatureThe mixture was warmed
temperatureto reflux temperature
temperatureAfter cooling
concentrationthe mixture was concentrated

Sources & evidence

ORD record: ord-b3634426cd34462daef678e69ac8331e
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544976B1

Reaction notes

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