Sodium periodate → HCID 178442553, compound

HRID 582181Notes

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): δ 1.3(6H,m), 1.7-1.9(2H,m), 2.4(3H,2 xs), 2.5-2.7(2H,m), 4.05(5H,m), 7.1-7.3(15H,m), 8.0(1H,2 xs).

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-aa5c9bb82eb046a8bf6aab797e9027a8
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922644

Reaction notes

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