tert-Butyldimethylsilyl chloride → HCID 18734916, compound

HRID 1934378Notes

Reaction equation

HRID 1934378 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:9]([C@H:11]1[NH:14][C:13](=[O:15])[CH2:12]1)#[CH:10]>ClCCl.C(N(C(C)C)C(C)C)C>[Si:1]([N:14]1[C@H:11]([C:9]#[CH:10])[CH2:12][C:13]1=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 11094543HCID 11094543, compound

Product 1

HCID 18734916HCID 18734916, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

tert-butyldimethylsilyl chloride (1.42 g) was added to a mixture of 4(S)-ethynyl-2-azetidinone (0.78 g) in dichloromethane (10 ml) and ethyldiisopropylamine (2.14 ml) at room temperature. The reaction mixture was stirred overnight, 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)-ethynyl-2-azetidinone (1.4 g) as a colorless oil.

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by column chromatography on silica gel eluting with n-hexane-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-7bd1c58b8d574e6d95a211a83096307d
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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