Sodium Thiosulfate → HCID 86704650, compound

HRID 1508601Notes

Reaction equation

HRID 1508601 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[O:13][C:12](=[O:14])[N:11]([CH2:15][C:16]3[C:21]([C:22]4[CH:23]=[C:24]([C:30]5[CH:35]=[CH:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[CH:32][C:31]=5[CH3:40])[CH:25]=[CH:26][C:27]=4[O:28][CH3:29])=[CH:20][N:19]=[C:18](SC)[N:17]=3)[C@H:10]2[CH3:43])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[C:45]1C=CC=C(C(OO)=O)C=1.[S:55]([O-:59])([O-])(=[O:57])=S.[Na+].[Na+]>C(Cl)Cl>[Cl:8][C:6]1[CH:5]=[C:4]([C@H:9]2[O:13][C:12](=[O:14])[N:11]([CH2:15][C:16]3[C:21]([C:22]4[CH:23]=[C:24]([C:30]5[CH:35]=[CH:34][C:33]([C:36]([O:38][CH3:39])=[O:37])=[CH:32][C:31]=5[CH3:40])[CH:25]=[CH:26][C:27]=4[O:28][CH3:29])=[CH:20][N:19]=[C:18]([S:55]([CH3:45])(=[O:59])=[O:57])[N:17]=3)[C@H:10]2[CH3:43])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86704647HCID 86704647, compound

Product 1

HCID 86704650HCID 86704650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To methyl 3′-[4-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-2-(methylsulfanyl)pyrimidin-5-yl]-4′-methoxy-2-methylbiphenyl-4-carboxylate (294 mg, 0.46 mmol) in DCM (5 mL) at 0° C. was added m-chloroperbenzoic acid (319 mg, 1.381 mmol). The reaction was allowed to warm to room temperature and was diluted with DCM and sat'd sodium thiosulfate solution. The organic was washed with sat'd NaHCO3, brine, dried (Na2SO4) concentrate before purification by column chromatography to yield methyl 3′-[4-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-2-(methylsulfonyl)pyrimidin-5-yl]-4′-methoxy-2-methylbiphenyl-4-carboxylate (292 mg, 0.435 mmol). LCMS calc.=670.2. found=670.2.

Workup

  1. washThe organic was washed with sat'd NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrate before purification by column chromatography

Sources & evidence

ORD record
ord-cf58f35c215f43d392421d7959efb0a9
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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