Methanol → HCID 9978975, compound

HRID 1452600Notes

Reaction equation

HRID 1452600 reaction equation
[S:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[N:24]=[N:23][C:22]([CH3:25])=[N:21]4)[O:16][C:15]3=[O:26])=[CH:9][C:8]=2[F:27])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:29].[Na+].CO>ClCCl>[O:29]=[S:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:8]([F:27])=[CH:9][C:10]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[N:24]=[N:23][C:22]([CH3:25])=[N:21]4)[O:16][C:15]3=[O:26])=[CH:11][C:12]=2[F:13])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 10069254HCID 10069254, compoundHCID 23667635Sodium periodate

Product 1

HCID 9978975HCID 9978975, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5R)-3-[4-(Tetrahydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[(5-methyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-one (Example 34) (0.53 g, 1.34 mmol) was oxidized with sodium periodate (0.314 g, 1.47 mmol) as described for Intermediates 42 and 43. Chromatography on silica gel with 0-5% methanol in dichloromethane gave a mixture together with the corresponding E-isomer, which was separated on a Chiracel OD chiral chromatography column using hexanes/isopropanol (1:1) as eluant to give the title compound (50 mg) as a colourless solid.

Workup

  1. customwas separated on a Chiracel OD chiral chromatography column

Sources & evidence

ORD record
ord-c3bfcf8af50b44b59b16ed9bec4a7ebd
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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