Ethyl Acetate → HCID 131728014, compound

HRID 1799764Notes

Reaction equation

HRID 1799764 reaction equation
[CH:1]([N:4]([CH:10]([CH3:12])[CH3:11])[C:5](=[O:9])[O:6][CH2:7]Cl)([CH3:3])[CH3:2].[OH:13][C@@H:14]([C@H:16]1[C:35](=[O:36])[N:18]2[C:19]([C:32]([O-:34])=[O:33])=[C:20]([S:22]/[CH:23]=[CH:24]\[C:25]3[S:29][CH:28]=[N:27][C:26]=3[CH2:30][OH:31])[CH2:21][C@H:17]12)[CH3:15].[Na+].C(OCC)(=O)C>CN(C)C(=O)C.[Cl-].[Na+].O>[OH:13][C@@H:14]([C@H:16]1[C:35](=[O:36])[N:18]2[C:19]([C:32]([O:34][CH2:7][O:6][C:5]([N:4]([CH:10]([CH3:12])[CH3:11])[CH:1]([CH3:3])[CH3:2])=[O:9])=[O:33])=[C:20]([S:22]/[CH:23]=[CH:24]\[C:25]3[S:29][CH:28]=[N:27][C:26]=3[CH2:30][OH:31])[CH2:21][C@H:17]12)[CH3:15]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 85789591HCID 85789591, compoundHCID 131728015HCID 131728015, compound

Product 1

HCID 131728014HCID 131728014, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
30 °C

Procedure

Chloromethyl N,N-diisopropylcarbamate (54 mg) and 75 mg of n-tetrabutyl ammonium bromide were added to 2 ml of a solution of 100 mg of sodium (5R,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylate in N,N-dimethylacetamide, and the mixture was stirred at 30° C. for 3.5 hr. Ethyl acetate (10 ml) and 10 ml of semi-saturated brine were added to the reaction solution, followed by separation. The organic layer was washed three times with 10 ml of semi-saturated brine, was dried over anhydrous magnesium sulfate, and was filtered. Ethyl acetate was removed by distillation under the reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:methanol=15:1) to give 108 mg of the title compound.

Workup

  1. customfollowed by separation
  2. washThe organic layer was washed three times with 10 ml of semi-saturated 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-63c438eb0d1c44d4a20c6b89d8c3a06d
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

Loading…