Ethyl Acetate → HCID 86596175, compound

HRID 1271107Notes

Reaction equation

HRID 1271107 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:14][C@H:13]3[N:10]([C:11](=[O:22])[C@@H:12]3[C@H:15]([O:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH3:16])[C:9]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[CH3:45][N:46]=[C:47]=[O:48].C(OCC)(=O)C>ClCCl>[CH3:45][NH:46][C:47]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:14][C@H:13]3[N:10]([C:11](=[O:22])[C@@H:12]3[C@H:15]([O:17][Si:18]([CH3:20])([CH3:21])[CH3:19])[CH3:16])[C:9]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH:5]=[CH:6][CH:7]=1)=[O:48]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 86596173HCID 86596173, compound

Product 1

HCID 86596175HCID 86596175, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-nitrobenzyl (5R,6S)-3-(3-hydroxyphenyl)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate prepared in the above step in dichloromethane (10 ml) was added N,N-diisopropylethylamine (catalytic amount), and thereto was added under ice cooling a solution of methyl isocyanate (57 mg) in dichloromethane (5 ml). After stirring under ice cooling for 2 hours, the temperature was raised to room temperature and the reaction mixture was poured into a mixture of ice water and ethyl acetate. The mixture was extracted and separated with a separating funnel. The organic layer was washed with cold water (twice) and a cold saturated aqueous sodium chloride solution in the order, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 4-nitrobenzyl (5R,6S)-3-(3-{[(methylamino)carbonyl]oxy}phenyl)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (276 mg).

Workup

  1. extractionThe mixture was extracted
  2. customseparated with a separating funnel
  3. washThe organic layer was washed with cold water (twice) and a cold saturated aqueous sodium chloride solution in the order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-08689797ee5e46289651bda42c344932
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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