Phenyl isocyanate → HCID 54382464, compound

HRID 1934379Notes

Reaction equation

HRID 1934379 reaction equation
C1(N=C=[O:9])C=CC=CC=1.[Si:10]([N:17]1[C@H:20]([C:21]#[CH:22])[CH2:19][C:18]1=[O:23])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].[CH2:24]([N:26](CC)CC)[CH3:25]>C1C=CC=CC=1.[N+](CC)([O-])=O>[Si:10]([N:17]1[C@H:20]([C:21]2[O:9][N:26]=[C:24]([CH3:25])[CH:22]=2)[CH2:19][C:18]1=[O:23])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 18734916HCID 18734916, compound

Product 1

HCID 54382464HCID 54382464, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 6587NitroethaneSolvent

Procedure

A solution of phenylisocyanate (0.93 ml) in benzene (5 ml) was added to a mixture of 1-tert-butyldimethylsilyl-4(S)-ethynyl-2-azetidinone (1.0 g) in benzene (10 ml), nitroethane (0.35 ml), and triethylamine (0.1 ml) in benzene (5 ml) at room temperature. The reaction mixture was refluxed for 8 hours, then evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with n-hexane-ethyl acetate (9:1) to give 1-tert-butyldimethylsilyl-4(S)-(3-methyl-5-isoxazolyl)-2-azetidinone (0.96 g) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. customevaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel eluting with n-hexane-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-4b1b7613e18146ad923babdea79490c8
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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