Acetonitrile → HCID 10364220, compound

HRID 1452592Notes

Reaction equation

HRID 1452592 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[CH:24]=[C:23]([CH3:25])[N:22]=[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+].C(#N)C>O>[F:13][C:12]1[CH:11]=[C:10]([N:14]2[CH2:18][C@H:17]([CH2:19][N:20]3[CH:24]=[C:23]([CH3:25])[N:22]=[N:21]3)[O:16][C:15]2=[O:26])[CH:9]=[C:8]([F:27])[C:7]=1[CH:4]1[CH2:5][CH2:6][S:1](=[O:29])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10318471HCID 10318471, compoundHCID 23667635Sodium periodate

Product 1

HCID 10364220HCID 10364220, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(5R)-3-[4-(Tetrahydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (Example 24) (1.0 g, 2.5 mmol) was oxidized with sodium periodate (0.6 g, 2.8 mmol) as described for Intermediates 42 and 43. Reverse Phase chromatography with 10-25% acetonitrile in water containing 0.1% trifluoroacetic acid gave the Z-isomer as the first eluting product (105 mg), followed by elution of the E-isomer (60 mg) of the title compound.

Sources & evidence

ORD record
ord-e609a22e51b444de97778da31f996a1c
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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