Tert-Butyl nitrite → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-bromo-5-(methylthio)benzyl]-4-methyl-1,3-oxazolidin-2-one

HRID 1994637Notes

Reaction equation

HRID 1994637 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([Br:30])=[C:6]([CH:29]=1)[CH2:7][N:8]1[C@@H:12]([CH3:13])[C@@H:11]([C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=2)[O:10][C:9]1=[O:28].N(OC(C)(C)C)=O.[CH3:38][S:39]SC>>[F:25][C:24]([F:27])([F:26])[C:16]1[CH:15]=[C:14]([C@H:11]2[O:10][C:9](=[O:28])[N:8]([CH2:7][C:6]3[CH:29]=[C:2]([S:39][CH3:38])[CH:3]=[CH:4][C:5]=3[Br:30])[C@H:12]2[CH3:13])[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=1

Participants

4

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl DisulfideHCID 59135200(4S,5R)-3-(5-amino-2-bromobenzyl)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 59135210(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-bromo-5-(methylthio)benzyl]-4-methyl-1,3-oxazolidin-2-one

Conditions

Temperature
80 °C

Procedure

To a solution of (4S,5R)-3-(5-amino-2-bromobenzyl)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (457 mg, 0.92 mmol) in methyl disulfide (4 mL) was added tert-butyl nitrite (182 μL, d=0.867, 1.38 mmol). The resulting mixture was stirred at 80° C. for 1 h. An aliquot indicated completion of the reaction. The titled compound was obtained as a glassy material after preparative TLC plates eluted by 25% EtOAc in hexanes. LC-MS: 529.71 (M+1)+.

Workup

  1. customcompletion of the reaction

Sources & evidence

ORD record
ord-60f0df5a2b4f467da0bb630869bad055
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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