(3S,4R)-3-[(1R)-1-hydroxyethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxo ethyl)-1-[4-nitrobenzyloxycarbonyl(triphenyl phosphoranylidene)methyl]azetidin-2-one → (4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate

HRID 2113298Notes

Reaction equation

HRID 2113298 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[C@@H:7]([C@@H:8]([CH3:27])[C:9]([C:11]2[S:15][C:14]3=[C:16]([C:19]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:20])[N:17]=[CH:18][N:13]3[CH:12]=2)=O)[N:6]([C:28]([C:48]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][CH:53]=2)=[O:49])=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:5]1=[O:61])[CH3:3]>C1(C)C=CC=CC=1>[OH:1][C@@H:2]([C@H:4]1[C:5](=[O:61])[N:6]2[C:28]([C:48]([O:50][CH2:51][C:52]3[CH:53]=[CH:54][C:55]([N+:58]([O-:60])=[O:59])=[CH:56][CH:57]=3)=[O:49])=[C:9]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:8]([CH3:27])[C@H:7]12)[CH3:3]

Participants

3

Reactant 1

HCID 86619388(3S,4R)-3-[(1R)-1-hydroxyethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxo ethyl)-1-[4-nitrobenzyloxycarbonyl(triphenyl phosphoranylidene)methyl]azetidin-2-one

Product 1

HCID 68934911(4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylateYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 46.9 mg of (3S,4R)-3-[(1R)-1-hydroxy 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 1 ml of toluene was heated under reflux for 3 hr. The solvent was removed by evaporation, and the residue was purified by thin layer chromatography (developed with 10% methanol/methylene chloride) to give 23.1 mg of (4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate.

Workup

  1. temperatureunder reflux for 3 hr
  2. customThe solvent was removed by evaporation
  3. customthe residue was purified by thin layer chromatography (developed with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-3b31f90b49b54e308563b4a61c27fa65
Source dataset
uspto-grants-2009_04
Patent number
US07524951B2

Reaction notes

Loading…