Sodium Carbonate → 4-Nitrobenzyl 2-(4-allylthio-3-ethylazetidin-2-on-1-yl)acetate

HRID 1381207Notes

Reaction equation

HRID 1381207 reaction equation
[CH2:1]([S:4][CH:5]1[N:8]([CH2:9][C:10]([OH:12])=[O:11])[C:7](=[O:13])[CH:6]1[CH2:14][CH3:15])[CH:2]=[CH2:3].C(=O)([O-])[O-].[Na+].[Na+].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23]>CC(N(C)C)=O>[CH2:1]([S:4][CH:5]1[N:8]([CH2:9][C:10]([O:12][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)=[O:11])[C:7](=[O:13])[CH:6]1[CH2:14][CH3:15])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 660114-Nitrobenzyl bromideHCID 13106496(4-Allylthio-3-ethylazetidin-2-on-1-yl)acetic acid

Product 1

HCID 131064974-Nitrobenzyl 2-(4-allylthio-3-ethylazetidin-2-on-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2.5 g of 2-(4-allylthio-3-ethylazetidin-2-on-1-yl)acetic acid, 8 ml of dimethylacetamide and 636 mg of anhydrous sodium carbonate was stirred under argon for 20 minutes, and then 2.59 g of 4-nitrobenzyl bromide were added. After 30 minutes further stirring, the mixture was partitioned between ethyl acetate and water. The organic layer was separated and was washed with saturated sodium bicarbonate, with water, with brine, was dried over MgSO4, and was evaporated in vacuo to dryness. Chromatography over silica gel, eluting with hexane-ethyl acetate mixtures, afforded the title compound as a pale yellow oil. (3.0 g)

Workup

  1. stirringAfter 30 minutes further stirring
  2. customthe mixture was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwas washed with saturated sodium bicarbonate, with water, with brine
  5. dry with materialwas dried over MgSO4
  6. customwas evaporated in vacuo to dryness
  7. washChromatography over silica gel, eluting with hexane-ethyl acetate mixtures

Sources & evidence

ORD record
ord-f794fd8c59fe4307b63103be382d11ff
Source dataset
uspto-grants-1986_04
Patent number
US04585767

Reaction notes

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