HCID 11957759, compound → HCID 11965220, compound

HRID 1009215Notes

Reaction equation

HRID 1009215 reaction equation
[C:1]1([NH:7][C:8]([O:10][CH2:11][C:12]2([CH2:24][O:25][C:26](=[O:34])[NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[CH3:23])[S:14][CH2:13]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=[O:36].[Na+]>CO.O>[C:28]1([NH:27][C:26]([O:25][CH2:24][C:12]2([CH2:11][O:10][C:8](=[O:9])[NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[CH3:23])[S:14](=[O:36])[CH2:13]2)=[O:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 11957759HCID 11957759, compoundHCID 23667635Sodium periodate

Product 1

HCID 11965220HCID 11965220, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 3,3-bis(phenylcarbamoyloxymethyl)-5-methylthiochroman-4-one (190 mg, 0.4 mmol) in MeOH (5 ml) was admixed with a solution of sodium metaperiodate (92 mg, 0.43 mmol) in water (1 ml), and stirred at RT for 72 h. The reaction mixture was diluted with water (50 ml) and extracted with EtOAc (3×30 ml), the combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. After column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc), the desired product was obtained as a white solid (190 mg, 89% of theory, m.p. 76-82° C.).

Workup

  1. extractionextracted with EtOAc (3×30 ml)
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customAfter column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-65d6b0319aef4ab6b89b0d739bb1940b
Source dataset
uspto-grants-2011_07
Patent number
US07973072B2

Reaction notes

Loading…