2-Piperidone → 2-(3-Methoxypropoxy)-N-{3-methyl-2(S)-[2-oxo-5(S)-(2-oxopiperidin-1-ylmethyl)-oxazolidin-4(S)-ylmethyl]butyl}benzamide

HRID 507851Notes

Reaction equation

HRID 507851 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7].CC(C)([O-])C.[K+].[CH3:14][O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:46]=[CH:45][CH:44]=[CH:43][C:21]=1[C:22]([NH:24][CH2:25][C@H:26]([CH:40]([CH3:42])[CH3:41])[CH2:27][C@H:28]([NH:32][C:33](=[O:39])[O:34]C(C)(C)C)[C@@H:29]1[CH2:31]O1)=[O:23]>CS(C)=O>[CH3:14][O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:46]=[CH:45][CH:44]=[CH:43][C:21]=1[C:22]([NH:24][CH2:25][C@@H:26]([CH2:27][C@H:28]1[C@H:29]([CH2:31][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]2=[O:7])[O:39][C:33](=[O:34])[NH:32]1)[CH:40]([CH3:42])[CH3:41])=[O:23]

Participants

5

Reactant 3

HCID 126652-PiperidoneHCID 23665647Potassium tert-butoxideHCID 86613450tert-butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)-(R)-oxiranylpentyl)-carbamate

Product 1

HCID 686239802-(3-Methoxypropoxy)-N-{3-methyl-2(S)-[2-oxo-5(S)-(2-oxopiperidin-1-ylmethyl)-oxazolidin-4(S)-ylmethyl]butyl}benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 0.115 g of piperidin-2-one, 0.136 g of potassium tert-butoxide in 3 ml of dimethyl sulphoxide is stirred at room temperature over 30 minutes, admixed with 0.26 g of tert-butyl (3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methyl-1(S)—(R)-oxiranylpentyl)-carbamate (Example 1b) and subsequently stirred further at room temperature overnight. The reaction mixture is poured onto ice-water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed successively with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified from the residue by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. stirringsubsequently stirred further at room temperature overnight
  2. additionThe reaction mixture is poured onto ice-water
  3. extractionextracted with tert-butyl methyl ether (2×)
  4. washThe combined organic phases are washed successively with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-787a7e4668c44104b35774cb236b783b
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

Loading…