Acetic-formic anhydride → methyl 2-[(3R,4R)-3-formamido-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719280Notes

Reaction equation

HRID 1719280 reaction equation
[NH2:1][C@@H:2]1[C@@H:5]([CH2:6][CH:7]=[CH2:8])[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3]1=[O:17].[CH:18](OC(=O)C)=[O:19]>ClCCl.C(OCC)(=O)C>[CH:18]([NH:1][C@@H:2]1[C@@H:5]([CH2:6][CH:7]=[CH2:8])[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3]1=[O:17])=[O:19]

Participants

5

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 14581224methyl [(3R,4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

Product 1

HCID 22823198methyl 2-[(3R,4R)-3-formamido-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-[(3R,4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (500 mg) in dichloromethane (5 ml) was added acetic formic anhydride (0.34 ml) at 0°. After stirring at the same temperature for one hour, the mixture was diluted with ethyl acetate (35 ml) and washed with a dilute aqueous sodium bicarbonate. The aqueous layer was saturated with sodium chloride and extracted with dichloromethane. The extracts were combined, washed with a saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (2.5 g) eluting with 10-30% acetone in dichloromethane afforded methyl 2-[(3R,4R)-3-formamido-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (485 mg).

Workup

  1. washwashed with a dilute aqueous sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. washwashed with a saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (2.5 g)
  7. washeluting with 10-30% acetone in dichloromethane

Sources & evidence

ORD record
ord-39053c7de7144c5da172acd2384c5b1f
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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