Allyl 2-[(3S,4R)-4-[(E)-4-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]-3-{(1R)-1-t-butyldimethylsilyloxyethyl}-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetate → allyl (5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1090545Notes

Reaction equation

HRID 1090545 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1/[CH:12]=[C:13](\[CH3:58])/[C:14](=O)[CH2:15][C@H:16]1[N:19]([C:20](=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[C:18](=[O:46])[C@@H:17]1[C@H:47]([O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[CH3:48])=[O:6])[CH:2]=[CH2:3]>C1(C)C(C)=CC=CC=1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1/[CH:12]=[C:13](/[C:14]1[CH2:15][C@H:16]2[N:19]([C:18](=[O:46])[C@@H:17]2[C@H:47]([O:49][Si:50]([C:53]([CH3:54])([CH3:56])[CH3:55])([CH3:51])[CH3:52])[CH3:48])[C:20]=1[C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])\[CH3:58])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 15702902Allyl 2-[(3S,4R)-4-[(E)-4-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]-3-{(1R)-1-t-butyldimethylsilyloxyethyl}-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetate

Product 1

HCID 15702903allyl (5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 82.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

Allyl 2-[(3S,4R)-4-[(E)-4-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]-3-{(1R)-1-t-butyldimethylsilyloxyethyl}-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetate (9.78 g) was dissolved in degassed xylene (150 ml) and the solution was heated to 150° C. for 10 hours. Evaporation of the mixture gave a residue, which was chromatographed on silica gel (250 ml) eluting with a mixture of n-hexane and ethyl acetate (2:8-7:3 V/V) to give allyl (5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-1-methylethenyl]-6-{(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (5.36 g).

Workup

  1. customEvaporation of the mixture
  2. customgave a residue, which
  3. customwas chromatographed on silica gel (250 ml)
  4. washeluting with a mixture of n-hexane and ethyl acetate (2:8-7:3 V/V)

Sources & evidence

ORD record
ord-cb6271da80264b0ab9215ac08077eb7f
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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