Sodium Iodide → p-Nitrobenzyl (4-methylthio-2-azetidinon-1-yl)acetate

HRID 980961Notes

Reaction equation

HRID 980961 reaction equation
[I-].[Na+].C([BH3-])#N.[Na+].Cl[CH:8]([N:22]1[CH:25]([S:26][CH3:27])[CH2:24][C:23]1=[O:28])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10]>CN(C)P(N(C)C)(N(C)C)=O>[CH3:27][S:26][CH:25]1[N:22]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:23](=[O:28])[CH2:24]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 5003444Sodium cyanoborohydrideHCID 20220789p-Nitrobenzyl 2-chloro-2-(4-methylthio-2-azetidinon-1-yl)acetate

Product 1

HCID 20220761p-Nitrobenzyl (4-methylthio-2-azetidinon-1-yl)acetateYield 59.3%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

Sodium iodide (687 mg) and sodium cyanoborohydride (576 mg) were added to a solution of crude p-nitrobenzyl 2-chloro-2-(4-methylthio-2-azetidinon-1-yl)acetate (1.58 g) in hexamethylphosphoramide (15 ml), and the resulting mixture was stirred at room temperature for an hour. The reaction mixture was then poured into ice-water and the precipitates produced were collected by filtration, washed with water, dried and recrystallized from ethyl acetate to afford 844 mg of the desired compound.

Workup

  1. customthe precipitates produced
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-955c0da1749e402f88f34b69c7c0a4de
Source dataset
uspto-grants-1987_01
Patent number
US04639441

Reaction notes

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