Pyridine → HCID 87589056, compound

HRID 230040Notes

Reaction equation

HRID 230040 reaction equation
N1C=CC=CC=1.[Si:7]([O:14][C@@H:15]([C@@H:17]1[C@@H:20]([C@@H:21]([CH3:40])[C:22]([C:24]2[S:28][C:27]3=[C:29]([C:32]([C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)=[O:33])[N:30]=[CH:31][N:26]3[CH:25]=2)=[O:23])[N:19]([CH:41]([C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])O)[C:18]1=[O:56])[CH3:16])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].S(Cl)([Cl:59])=O>O1CCCC1.C(OCC)(=O)C>[Si:7]([O:14][C@@H:15]([C@@H:17]1[C@@H:20]([C@@H:21]([CH3:40])[C:22]([C:24]2[S:28][C:27]3=[C:29]([C:32]([C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)=[O:33])[N:30]=[CH:31][N:26]3[CH:25]=2)=[O:23])[N:19]([CH:41]([C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])[Cl:59])[C:18]1=[O:56])[CH3:16])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 68820818HCID 68820818, compound

Product 1

HCID 87589056HCID 87589056, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

Pyridine (0.1 ml) was added to a solution of 0.23 g of the crude product 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-nitrobenzyloxy)carbonyl]hydroxymethyl]azetidin-2-one in 2 ml of tetrahydrofuran under an argon atmosphere, and the mixture was cooled to −20° C. Thionyl chloride (0.09 ml) was added thereto, and the mixture was stirred at that temperature for one hr. The reaction mixture was diluted with ethyl acetate, and the diluted reaction mixture was washed with water and saturated brine and was then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation to give a crude product 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-nitrobenzyloxy)carbonyl]chloromethyl]azetidin-2-one. Triphenylphosphine (0.26 g) and 0.05 g of potassium iodide were added to a solution of this crude product in 2 ml of dimethylformamide, and the mixture was stirred at 60° C. for one hr. The reaction mixture was diluted with ethyl acetate, and the diluted reaction mixture was washed with water and saturated brine and was then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by thin layer chromatography (developed with 10% methanol/ethyl acetate) to give 0.19 g 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.

Workup

  1. customthe diluted reaction mixture
  2. washwas washed with water and saturated brine
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-63d8325547274fb3ad3e8ebbe436cf3b
Source dataset
uspto-grants-2009_07
Patent number
US07563901B2

Reaction notes

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