Hydrochloric Acid → (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

HRID 230042Notes

Reaction equation

HRID 230042 reaction equation
Cl.[Si]([O:9][C@@H:10]([C@@H:12]1[C@@H:15]([C@@H:16]([CH3:35])[C:17]([C:19]2[S:23][C:22]3=[C:24]([C:27]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:28])[N:25]=[CH:26][N:21]3[CH:20]=2)=[O:18])[N:14]([C:36]([C:56]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][C:63]([N+:66]([O-:68])=[O:67])=[CH:62][CH:61]=2)=[O:57])=[P:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:13]1=[O:69])[CH3:11])(C(C)(C)C)(C)C.C(=O)(O)[O-].[Na+]>CO>[OH:9][C@@H:10]([C@@H:12]1[C@@H:15]([C@@H:16]([CH3:35])[C:17]([C:19]2[S:23][C:22]3=[C:24]([C:27]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:28])[N:25]=[CH:26][N:21]3[CH:20]=2)=[O:18])[N:14]([C:36]([C:56]([O:58][CH2:59][C:60]2[CH:61]=[CH:62][C:63]([N+:66]([O-:68])=[O:67])=[CH:64][CH:65]=2)=[O:57])=[P:37]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:13]1=[O:69])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 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 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-oneYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5 N aqueous hydrochloric acid solution (1 ml) was added to a solution of 72.4 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 methanol, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by thin layer chromatography (developed with 10% methanol/methylene chloride) to give 46.9 mg of (3S,4R)-3-[(1R)-1-hydroxyethyl]-4-{(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl}-1-[4-nitrobenzyloxycarbonyl(triphenyl phosphoranylidene)methyl]azetidin-2-one.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by evaporation
  5. customthe residue was purified by thin layer chromatography (developed with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-e36a61e4244247bf9e16eb28e2df63ac
Source dataset
uspto-grants-2009_07
Patent number
US07563901B2

Reaction notes

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