Ethyl Bromide → Diethyl (R)-(2-(4-benzyl-2-oxooxazolidin-3-yl)-2-oxoethyl)phosphonate

HRID 736920Notes

Reaction equation

HRID 736920 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:17])[CH2:15]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:20][P:21]([O:25]CC)[O:22][CH2:23][CH3:24])[CH3:19].C(Br)C>>[CH2:18]([O:20][P:21]([CH2:15][C:14]([N:9]1[C@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:17])(=[O:25])[O:22][CH2:23][CH3:24])[CH3:19]

Participants

4

Reactant 3

HCID 6332Ethyl BromideHCID 31215Triethyl phosphiteHCID 118086442-Oxazolidinone, 3-(bromoacetyl)-4-(phenylmethyl)-, (4R)-

Product 1

HCID 11187374Diethyl (R)-(2-(4-benzyl-2-oxooxazolidin-3-yl)-2-oxoethyl)phosphonate

Procedure

A solution of 168.0 g (0.56 mol) (R)-4-benzyl-3-(2-bromo-acetyl)-oxazolidin-2-one and 188.6 mL (1.1 mol) of triethylphosphite was stirred for 1.5 h at 60° C., while the ethylbromide formed was distilled off. The reaction mixture was concentrated by evaporation i. vac. and the residue remaining was purified by chromatography on silica gel. The desired product was obtained in the form of a yellowish-brown oil.

Workup

  1. customformed
  2. distillationwas distilled off
  3. concentrationThe reaction mixture was concentrated by evaporation i
  4. customand the residue remaining was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-79ad2354fe634f50857badcb6b35f6fa
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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