HCID 15117215, compound → HCID 15117351, compound

HRID 1029681Notes

Reaction equation

HRID 1029681 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH:11]=[C:10]([C:13](=O)[CH2:14][C@H:15]2[N:18]([C:19](=P(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[C:17](=[O:45])[C@@H:16]2[C@H:46]([O:48][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])[CH3:47])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH:11]=[C:10]([C:13]2[CH2:14][C@H:15]3[N:18]([C:17](=[O:45])[C@@H:16]3[C@H:46]([O:48][Si:49]([C:52]([CH3:53])([CH3:54])[CH3:55])([CH3:51])[CH3:50])[CH3:47])[C:19]=2[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 15117215HCID 15117215, compound

Product 1

HCID 15117351HCID 15117351, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Allyl 2-[(3S,4R)-4-{2-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl}-3-{(1R)-1-t-butyldimethylsilyloxyethyl}-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetate (2.0 g) was dissolved in degassed toluene (40 ml) and the solution was heated to reflux for 8 hours. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (50 g) eluting with a mixture of n-hexane and ethyl acetate (19:1-7:3 V/V) to give allyl (5R,6S)-3-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.94 g).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 8 hours
  3. customEvaporation of the solvent
  4. customgave a residue, which
  5. customwas chromatographed on silica gel (50 g)
  6. washeluting with a mixture of n-hexane and ethyl acetate (19:1-7:3 V/V)

Sources & evidence

ORD record
ord-023da9c67c264cdda38af90b5fbaba4d
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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