Vinyl Acetate → HCID 54306149, compound

HRID 843729Notes

Reaction equation

HRID 843729 reaction equation
[OH:1][CH2:2][N:3]1[CH:6]([C:7]#[C:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][C:4]1=[O:13].C(OC=C)(=O)C>ClCCl>[OH:1][CH2:2][N:3]1[C@@H:6]([C:7]#[C:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][C:4]1=[O:13]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 11816448HCID 11816448, compound

Product 1

HCID 54306149HCID 54306149, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
37 °C

Procedure

To a solution of N-hydroxymethyl-4-(2-trimethylsilylethynyl)-2azetidinone (250 g) in dichloromethane (6.5 L) was added vinyl acetate (350 ml) and Lipase PS (trademark; Amano Pharmaceutical Co., Ltd.) (190 g). The mixture was warmed to 37° C. and stirred for 32 hours. Catalyst was filtered off and washed with dichloromethane. Solvent was evaporated in vacuo. The residue was subjected to silica gel column chromatography eluting with (n-hexane:EtOAc=8:2 to 0:1) to give (R)-N-hydroxymethyl-4-(2-trimethylsilylethynyl)-2-azetidinone (192 g).

Workup

  1. filtrationCatalyst was filtered off
  2. washwashed with dichloromethane
  3. customSolvent was evaporated in vacuo
  4. washeluting with (n-hexane:EtOAc=8:2 to 0:1)

Sources & evidence

ORD record
ord-6040ea8713954358b149ab9e4fadca06
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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