Formic Acid → HCID 56626542, compound

HRID 1719300Notes

Reaction equation

[CH3:1][C:2]([CH3:19])=[C:3]([N:8]1[C@H:11]([CH2:12][CH:13]=[CH2:14])[C@@H:10]([CH:15]([OH:17])[CH3:16])[C:9]1=[O:18])[C:4]([O:6][CH3:7])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:39](O)=[O:40].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[CH3:19][C:2]([CH3:1])=[C:3]([N:8]1[C@H:11]([CH2:12][CH:13]=[CH2:14])[C@@H:10]([C@H:15]([O:17][CH:39]=[O:40])[CH3:16])[C:9]1=[O:18])[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A 1:3 mixture of methyl 3-methyl-2-[(3S,4R)-3-[(1RS)-1-hydroxyethyl]-2-oxo-4-allylazetidin-1-yl]but-2-enoate (55 mg) was dissolved in tetrahydrofuran (2 ml) and triphenylphosphine (135 mg) and formic acid (19.4 μl) were added to the mixture. This mixture was cooled to 0° C. and a solution of diethyl azodicarboxylate (81 μl) in tetrahydrofuran (1 ml) was added. After stirring at the same temperature overnight, the mixture was diluted with ethyl acetate (30 ml), washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (5 g) eluting with hexane and ethyl acetate (10:1-2:1) to give 25 mg of methyl 3-methyl-2-[(3S,4R)-3-[(1R)-1-formyloxyethyl]-2-oxo-4-allylazetidin-1-yl]-but-2-enoate.

Workup

washwashed with aqueous sodium bicarbonate and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was chromatographed on silica gel (5 g)
washeluting with hexane and ethyl acetate (10:1-2:1)

Sources & evidence

ORD record: ord-866396191d3a4fbc9c5c6d4ba42921be
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539152

Reaction notes

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