Periodate → HCID 22870610, compound

HRID 975847Notes

Reaction equation

HRID 975847 reaction equation
[CH2:1]([S:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH:17]([C@@H:19]1[C@:36]2([CH3:37])[C@H:22]([C@H:23]3[C@H:33]([CH2:34][CH2:35]2)[C@:31]2([CH3:32])[C@H:26]([N:27]([CH3:39])[C:28](=[O:38])[CH2:29][CH2:30]2)[CH2:25][CH2:24]3)[CH2:21][CH2:20]1)[CH3:18])=[O:15])[CH3:2].I([O-])(=O)(=O)=[O:41].[Na+].I([O-])(=O)(=O)=O>CC(C)=O.O>[CH2:1]([S:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH:17]([C@@H:19]1[C@:36]2([CH3:37])[C@H:22]([C@H:23]3[C@H:33]([CH2:34][CH2:35]2)[C@:31]2([CH3:32])[C@H:26]([N:27]([CH3:39])[C:28](=[O:38])[CH2:29][CH2:30]2)[CH2:25][CH2:24]3)[CH2:21][CH2:20]1)[CH3:18])=[O:15])=[O:41])[CH3:2]

Participants

6

Reactant 3

HCID 167232PeriodateHCID 9807943HCID 9807943, compoundHCID 23667635Sodium periodate

Product 1

HCID 22870610HCID 22870610, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 20-(11-(ethylthio)undecanoyloxy)-4-methyl-5α-4-azapregnan-3-one (0.056 g, 0.1 mM) in acetone (5 mL) at room temperature was added a solution of sodium periodate (0.033 mg, 0.154mM) in water (3 drops). After prolonged stirring with additional portions of the periodate added (0.046 g total) over 3 days, the solvents were removed in vacuo, and the residue extracted with methylene chloride. The methylene chloride was removed in vacuo, and the resulting residue was flash chromatographed on silica gel (30% acetone/methylene chloride eluant) to give the title compound as a glaze. MS M+ calculated for C34H59NO4S, mw=577.90; observed m/e 577.

Workup

  1. additionadded (0.046 g total) over 3 days
  2. customthe solvents were removed in vacuo
  3. extractionthe residue extracted with methylene chloride
  4. customThe methylene chloride was removed in vacuo
  5. customchromatographed on silica gel (30% acetone/methylene chloride eluant)

Sources & evidence

ORD record
ord-c3fedf39dd9344dcad73fe42ea710b03
Source dataset
uspto-grants-1997_03
Patent number
US05610162

Reaction notes

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