(3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl}-1-[4-nitrobenzyloxycarbonyl(triphenylphosphoranylidene)-methyl]azetidin-2-one → (4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate

HRID 2113296Notes

Reaction equation

HRID 2113296 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:34])[C:16]([C:18]2[S:22][C:21]3=[C:23]([C:26]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:27])[N:24]=[CH:25][N:20]3[CH:19]=2)=O)[N:13]([C:35]([C:55]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][C:62]([N+:65]([O-:67])=[O:66])=[CH:61][CH:60]=2)=[O:56])=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:12]1=[O:68])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:12](=[O:68])[N:13]2[C:35]([C:55]([O:57][CH2:58][C:59]3[CH:64]=[CH:63][C:62]([N+:65]([O-:67])=[O:66])=[CH:61][CH:60]=3)=[O:56])=[C:16]([C:18]3[S:22][C:21]4=[C:23]([C:26]([C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)=[O:27])[N:24]=[CH:25][N:20]4[CH:19]=3)[C@H:15]([CH3:34])[C@H:14]12)[CH3:10])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 86619389(3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl}-1-[4-nitrobenzyloxycarbonyl(triphenylphosphoranylidene)-methyl]azetidin-2-one

Product 1

HCID 131727433(4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylateYield 72.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 54.6 mg of (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl}-1-[4-nitrobenzyloxycarbonyl(triphenylphosphoranylidene)methyl]azetidin-2-one in 2 ml of toluene was heated under reflux for 2.5 hr. The solvent was removed by evaporation, and the residue was purified by thin layer chromatography (developed with 5% methanol/ethyl acetate) to give 28.3 mg of (4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate.

Workup

  1. temperatureunder reflux for 2.5 hr
  2. customThe solvent was removed by evaporation
  3. customthe residue was purified by thin layer chromatography (developed with 5% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-96977d7ae15f4132b42f5b1f3bd3e8da
Source dataset
uspto-grants-2009_04
Patent number
US07524951B2

Reaction notes

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