Acetamide, 2-(triphenylphosphoranylidene)- → HCID 18607031, compound

HRID 1709377Notes

Reaction equation

HRID 1709377 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[CH2:5][N:6]1[C@H:9]([CH:10]=O)[C@H:8]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:7]1=[O:20].[C:27]([CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:29])[NH2:28]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[CH2:5][N:6]1[C@@H:9](/[CH:10]=[CH:30]/[C:27](=[O:29])[NH2:28])[C@@H:8]([NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[C:7]1=[O:20]

Participants

4

Reactant 2

HCID 38099Acetamide, 2-(triphenylphosphoranylidene)-HCID 15058115HCID 15058115, compound

Product 1

HCID 18607031HCID 18607031, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.0 g (11 mmol) of t-butyl (3S,4S)-1-(2,4-dimethoxybenzyl)-4-formyl-2-oxo-3-azetidinecarbamate are dissolved in 300 ml of methylene chloride and the solution obtained is treated dropwise with a solution of 3.9 g (12 mmol) of carbamoylmethylene-triphenylphosphorane in 100 ml of methylene chloride. After 1 hour, the mixture is filtered and the crystals obtained are washed with methylene chloride. There are obtained 3.6 g (81%) of t-butyl (3R,4S)-1-(2,4-dimethoxybenzyl)-4-[(E)-2-carbamoylvinyl]-2-oxo-3-azetidinecarbamate of melting point 270° C.

Workup

  1. customthe solution obtained
  2. filtrationthe mixture is filtered
  3. customthe crystals obtained
  4. washare washed with methylene chloride

Sources & evidence

ORD record
ord-736a947ec70e40cca5c7bed2cf0ee259
Source dataset
uspto-grants-1990_08
Patent number
US04948898

Reaction notes

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