Ethyl Acetate → HCID 58844408, compound

HRID 1271110Notes

Reaction equation

HRID 1271110 reaction equation
[NH2:1][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:18][C@H:17]3[N:14]([C:15](=[O:22])[C@@H:16]3[C@H:19]([OH:21])[CH3:20])[C:13]=2[C:23]([O-:25])=[O:24])=[CH:8][CH:7]=1)=[O:3].[Na+].C(N(CC)C(C)C)(C)C.[C:36]([O:42][CH2:43]Cl)(=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38].C(OCC)(=O)C>CN(C)C=O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[NH2:1][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:18][C@H:17]3[N:14]([C:15](=[O:22])[C@@H:16]3[C@H:19]([OH:21])[CH3:20])[C:13]=2[C:23]([O:25][CH2:43][O:42][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[O:24])=[CH:8][CH:7]=1)=[O:3]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 87885Chloromethyl pivalateHCID 58844423HCID 58844423, compound

Product 1

HCID 58844408HCID 58844408, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of sodium (5R,6S)-3-(4-{[(aminocarbonyl)oxy]methyl}phenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (13 mg) in dry dimethylformamide (0.5 ml) was cooled with ice, and thereto were added N,N-diisopropylethylamine (5 mg), benzyltriethylammonium chloride (5 mg) and pivaloyloxymethyl chloride (11 mg). The mixture was gradually warmed to room temperature and stirred for overnight. To the reaction mixture were added ethyl acetate and ice water to separate by a separating funnel. The organic layer was washed with cold water (three times) and a cold saturated aqueous sodium chloride solution (twice), and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel thin-layer chromatography (ethyl acetate) to give [(2,2-dimethylpropanoyl)oxy]methyl (5R,6S)-3-(4-{[(aminocarbonyl)oxy]methyl}phenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (9.2 mg).

Workup

  1. customto separate by a separating funnel
  2. washThe organic layer was washed with cold water (three times)
  3. dry with materiala cold saturated aqueous sodium chloride solution (twice), and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel thin-layer chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-083ea40ed1314e12a1b0befbe033949e
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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