2,6-Lutidine → methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719281Notes

Reaction equation

N1C(C)=CC=CC=1C.P(Cl)(Cl)(Cl)=O.[CH:14]([NH:16][C@@H:17]1[C@@H:20]([CH2:21][CH:22]=[CH2:23])[N:19]([C:24](=[C:29]([CH3:31])[CH3:30])[C:25]([O:27][CH3:28])=[O:26])[C:18]1=[O:32])=O.C(OCC)(=O)C>ClCCl.[Cl-].[Na+].O>[N+:16]([C@@H:17]1[C@@H:20]([CH2:21][CH:22]=[CH2:23])[N:19]([C:24](=[C:29]([CH3:31])[CH3:30])[C:25]([O:27][CH3:28])=[O:26])[C:18]1=[O:32])#[C-:14]

Participants

Conditions

Temperature: 0 °C

Procedure

2,6-Lutidine (3.82 ml) and phosphorus oxychloride (1.37 ml) were added to a solution of methyl 2-[(3R,4R)-3-formamido-2-oxo-4-allylazetidin-1yl]-3-methylbut-2-enoate (970 mg) in dichloromethane (10 ml) at 0° C., and the mixture was stirred for three hours at 0° C. Then, the reaction mixture was poured into a mixture of ethyl acetate (100 ml) and brine (50 ml). The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The oily residue was chromategraphed on silica gel (15 g) eluting with a mixture of hexane and ethyl acetate (10:1-3:1) to give methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (766 mg) as an oil.

Workup

washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
washeluting with a mixture of hexane and ethyl acetate (10:1-3:1)

Sources & evidence

ORD record: ord-fe74a1f0aa514620a2fc2b8a03bf91b1
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539152

Reaction notes

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