Formic Acid → HCID 56626542, compound

HRID 851394Notes

Reaction equation

HRID 851394 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

7

Reactant 4

HCID 284Formic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70447946HCID 70447946, compound

Product 1

HCID 56626542HCID 56626542, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

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

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

Sources & evidence

ORD record
ord-2fed18bd14354b61b6dc675d874b497b
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

Loading…