Ethyl Acetate → HCID 69204198, compound

HRID 2376669Notes

Reaction equation

HRID 2376669 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[C:8]2[C:12]([O-:14])=[O:13])[CH3:3].[Na+].[CH3:24][CH:25](Cl)[O:26][C:27]([O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:28].C(OCC)(=O)C>CN(C=O)C.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)=[C:8]2[C:12]([O:14][CH:25]([O:26][C:27]([O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:28])[CH3:24])=[O:13])[CH3:3]

Participants

6

Reactant 3

HCID 8857Ethyl Acetate3×HCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 58691114HCID 58691114, compound

Product 1

HCID 69204198HCID 69204198, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(4-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.43 g) was dissolved in dry DMF (4.3 ml) and thereto was added triethylbenzylammonium chloride (0.25 g). Thereto was dropped 1-chloroethylcyclohexylcarbonate (0.62 g) and the mixture was stirred under heating to 50° C. One hour later, the mixture was cooled to room temperature and thereto was added ethyl acetate. The mixture was washed with bicarbonate solution, water and brine, successively. The organic layer was dried over sodium sulfate, concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2→1:3→ethyl acetate only) to give 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl(5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(4-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.12 g, yield 20%).

Workup

  1. temperatureOne hour later, the mixture was cooled to room temperature
  2. washThe mixture was washed with bicarbonate solution, water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified with silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-875b3bfe2f734f25905c9f93fb67173d
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

Loading…