Methanol → methyl 3-(3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-2-oxo-1,3-oxazinan-6-yl)propanoate

HRID 470546Notes

Reaction equation

HRID 470546 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C:13]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])([CH:16]([CH3:18])[CH3:17])[O:12][C:11]2=[O:24])[CH3:9])=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:29]O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C:13]([CH2:19][CH2:20][C:21]([O:23][CH3:29])=[O:22])([CH:16]([CH3:17])[CH3:18])[O:12][C:11]2=[O:24])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 596357833-(3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-2-oxo-1,3-oxazinan-6-yl)propanoic acid

Product 1

HCID 59635672methyl 3-(3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-2-oxo-1,3-oxazinan-6-yl)propanoateYield 96%

Procedure

To a solution of 3-(3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-2-oxo-1,3-oxazinan-6-yl)propanoic acid (41 mg, 0.1 mmol) in MeOH (10 mL) was added SOCl2 (5 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 h, concentrated, and purified by preparative TLC to give methyl 3-(3-((S)-1-(4-bromophenyl)ethyl)-6-isopropyl-2-oxo-1,3-oxazinan-6-yl)propanoate (42 mg, 96% yield).

Workup

  1. concentrationconcentrated
  2. custompurified by preparative TLC

Sources & evidence

ORD record
ord-d6fca24040c94c7289f9c9e6104c902c
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

Loading…