HCID 10185185, compound → HCID 10301225, compound

HRID 2185959Notes

Reaction equation

[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([N:16]2[C@H:20]([C@H:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)[OH:22])[CH2:19][S:18][CH2:17]2)=[O:15])=[CH:9][CH:8]=1)=[O:4].I([O-])(=O)(=O)=[O:34].[Na+]>CO.O>[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]([NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14]([N:16]2[C@H:20]([C@H:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)[OH:22])[CH2:19][S:18](=[O:34])[CH2:17]2)=[O:15])=[CH:11][CH:12]=1)=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4(R)-[(3,4-dichlorophenyl)-(S)hydroxymethyl]-thiazolidine-3-carboxylic acid {4-[(2,2-dimethyl-propionylamino)-methyl]-phenyl}-amide (11 mg, 0.022 mmol) in MeOH (2 ml) is added sodium periodate (4.9 mg, 0.023 mmol) in water (0.5 ml). The reaction mixture is stirred at 25° C. for 18 hrs. More aqueous sodium periodate is added by portions until almost complete conversion of the starting material. The reaction mixture is filtered on cellite and concentrated in vacuo. The residue is taken into methylene chloride, washed with water and brine, concentrated and purified by preparative reverse phase HPLC and flash chromatography (silica gel, 2% to 5% MeOH/NH3 in methylene chloride) sequentially to give the following two products isomeric at the sulfoxide center:

Workup

filtrationThe reaction mixture is filtered on cellite
concentrationconcentrated in vacuo
washwashed with water and brine
concentrationconcentrated
custompurified by preparative reverse phase HPLC and flash chromatography (silica gel, 2% to 5% MeOH/NH3 in methylene chloride) sequentially

Sources & evidence

ORD record: ord-fc3aa823b3fd4d47b35ca9d8a653772c
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403612B2

Reaction notes

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