Sodium periodate → HCID 178442553, compound

HRID 275563Notes

Reaction equation

[PH:1](=[O:4])([OH:3])[OH:2].[CH2:5]([C:7]([CH2:36][CH3:37])([CH:9]([S:34][CH3:35])[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:6].I([O-])(=O)(=O)=[O:39].[Na+]>CO.O>[PH:1](=[O:2])([OH:4])[OH:3].[CH2:36]([C:7]([CH2:5][CH3:6])([CH:9]([S:34]([CH3:35])=[O:39])[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:37]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of diethyl 3-methylthio-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.53 g, prepared as described in Example 39) in methanol (7 ml) was added slowly to a stirred solution of sodium periodate (0.23 g) in water (3 ml) cooled to 5° C. After ten minutes, the cooling bath was removed and stirring continued for a further five hours. The mixture was poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulphate, and evaporated under reduced pressure to give diethyl 3-methanesulphinyl-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.59 g, white gum) as a 2:1 mixture of diastereoisomers. NMR (CDCl3): δ1.3(6H,m), 1.7-1.9(2H,m), 2.4(3H,2xs), 2.5-2.7(2H,m), 4.05(5H,m), 7.1-7.3(15H,m), 8.0(1H,2xs).

Workup

waitAfter ten minutes
customthe cooling bath was removed
additionThe mixture was poured into water
extractionextracted with ethyl acetate
washThe extracts were washed with brine
dry with materialdried over magnesium sulphate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-a65888179e234d6b9f03f6ffdb9d04d6
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05393732

Reaction notes

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