Potassium Carbonate → HCID 70407642, compound

HRID 1381212Notes

Reaction equation

HRID 1381212 reaction equation
[CH2:1]([S:4][C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([CH3:19])([CH3:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:11])[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>CN(C=O)C>[CH2:1]([S:4][C@H:5]1[N:8]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([CH3:19])([CH3:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:11])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 10590430HCID 10590430, compound

Product 1

HCID 70407642HCID 70407642, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.76 g of 4(R)-allylthio-3(S)-[1(R)-{dimethyl-(2-methylprop-2-yl)silyloxy}ethyl]azetidin-2-one in 60 ml dry DMF were added 3.52 g of finely ground K2CO3 and 0.6 ml of methyl bromoacetate. After 18 hours, the mixture was filtered and then partitioned between ethyl acetate and water. The separated organic layer was washed with water and dried over MgSO4. Evaporation in vacuo afforded a crude product which was chromatographed on silica gel. Elution with ethyl acetate-hexane mixtures afforded 1.56 g of the title compound as a pale yellow oil.

Workup

  1. filtrationthe mixture was filtered
  2. custompartitioned between ethyl acetate and water
  3. washThe separated organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. customEvaporation in vacuo
  6. customafforded a crude product which
  7. customwas chromatographed on silica gel
  8. washElution with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-88aee41983594ff398ceba6d5d5ac4fe
Source dataset
uspto-grants-1986_04
Patent number
US04585767

Reaction notes

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