HCID 57643889, compound → HCID 57643907, compound

HRID 230045Notes

Reaction equation

HRID 230045 reaction equation
[CH2:1]([O:4][C:5]([C:7](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[N:8]1[C@H:11]([C@@H:12]([CH3:31])[C:13]([C:15]2[S:19][C:18]3=[C:20]([C:23]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)=[O:24])[N:21]=[CH:22][N:17]3[CH:16]=2)=O)[C@@H:10]([C@H:32]([OH:34])[CH3:33])[C:9]1=[O:35])=[O:6])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1>[OH:34][C@@H:32]([C@H:10]1[C:9](=[O:35])[N:8]2[C:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[C:13]([C:15]3[S:19][C:18]4=[C:20]([C:23]([C:25]5[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=5)=[O:24])[N:21]=[CH:22][N:17]4[CH:16]=3)[C@H:12]([CH3:31])[C@H:11]12)[CH3:33]

Participants

3

Reactant 1

HCID 57643889HCID 57643889, compound

Product 1

HCID 57643907HCID 57643907, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (20 ml) was added to 0.76 g of (3S,4R)-1-[allyloxycarbonyl(triphenylphosphoranylidene)methyl]-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl]azetidin-2-one, and the mixture was heated under reflux for 2 hr. The reaction solution was concentrated by removing the solvent, and the concentrate was purified by column chromatography on silica gel (eluted with 5 to 10% methanol/ethyl acetate). The eluate containing the contemplated product was concentrated, and the resultant solid was washed with a hexane:ethyl acetate=1:1 solution to give 0.38 g of allyl (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. This product was analyzed by NMR. The results were in agreement with the results of analysis in Example 26.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction solution was concentrated
  4. customby removing the solvent
  5. customthe concentrate was purified by column chromatography on silica gel (eluted with 5 to 10% methanol/ethyl acetate)
  6. additionThe eluate containing the contemplated product
  7. concentrationwas concentrated
  8. washthe resultant solid was washed with a hexane

Sources & evidence

ORD record
ord-d456bd3bb7b443b8afebd7476d4ce2ac
Source dataset
uspto-grants-2009_07
Patent number
US07563901B2

Reaction notes

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