Ethyl Acetate → HCID 68601674, compound

HRID 1799743Notes

Reaction equation

HRID 1799743 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O-:23])=[O:22])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[S:18][CH:17]=[N:16][C:15]=3[CH2:19][OH:20])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+].[CH3:27][C@H:28]1[CH2:33][CH2:32][CH2:31][C@@H:30]([CH3:34])[N:29]1[C:35]([O:37][CH2:38]Cl)=[O:36].C(OCC)(=O)C>CS(C)=O.[Cl-].[Na+].O>[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O:23][CH2:38][O:37][C:35]([N:29]3[C@H:30]([CH3:34])[CH2:31][CH2:32][CH2:33][C@@H:28]3[CH3:27])=[O:36])=[O:22])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[S:18][CH:17]=[N:16][C:15]=3[CH2:19][OH:20])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23676797Sodium (1r,5s,6s)-6-((1r)-1-hydroxyethyl)-2-[[(z)-2-(4-hydroxymethyl-thiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylateHCID 66648650HCID 66648650, compound

Product 1

HCID 68601674HCID 68601674, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate (300 mg) was added to 5 ml of a solution of 183 mg of (cis-2,6-dimethylpiperidin-1-yl)carbonyloxymethyl chloride in DMSO, and the mixture was stirred at room temperature for 18 hr. Ethyl acetate (20 ml) and 20 ml of 20% brine were added thereto, followed by separation. The organic layer was washed twice with 20% brine, was dried over anhydrous magnesium sulfate, and was filtered, and ethyl acetate was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=15:1) to give 273 mg of the title compound.

Workup

  1. customfollowed by separation
  2. washThe organic layer was washed twice with 20% brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationwas filtered
  5. customethyl acetate was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=15:1)

Sources & evidence

ORD record
ord-4f5da134f94d494696b7bf726a0084b4
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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