Sodium periodate → 20-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-phenylsulfinylpregna-5,7-diene

HRID 1587618Notes

Reaction equation

HRID 1587618 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][CH:8]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24]([CH2:25][C@@H:26]([O:41][C:42]([O:44][CH3:45])=[O:43])[CH2:27][C@@H:28]2[O:36][C:37]([O:39][CH3:40])=[O:38])=[CH:23][CH:22]=3)[CH2:19][CH2:18]1)[CH2:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1.C(OCC)C>[CH3:7][CH:8]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24]([CH2:25][C@@H:26]([O:41][C:42]([O:44][CH3:45])=[O:43])[CH2:27][C@@H:28]2[O:36][C:37]([O:39][CH3:40])=[O:38])=[CH:23][CH:22]=3)[CH2:19][CH2:18]1)[CH2:9][S:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:2]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 6778822120-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-phenylthiopregna-5, 7-diene

Product 1

HCID 6778888420-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-phenylsulfinylpregna-5,7-dieneYield 68.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 20 mg of sodium metaperiodate in 2 ml of tetrahydrofuran was added dropwise an ice-cooled solution of 41 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-phenylthiopregna-5,7-diene in 1 ml of diethyl ether. The resulting mixture was stirred with ice cooling for 30 minutes, then the insoluble matter was filtered off and washed with diethyl ether, and the filtrate and washings were combined, washed in sequence with an aqueous solution of sodium thiosulfate, water, an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium chloride, then dried and concentrated. The residue was purified by silica gel column chromatography to give 29 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-phenylsulfinylpregna-5,7 -diene.

Workup

  1. filtrationthe insoluble matter was filtered off
  2. washwashed with diethyl ether
  3. washwashed in sequence with an aqueous solution of sodium thiosulfate, water
  4. dry with materialan aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium chloride, then dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-78c82197c03d4f0a94b8256efa81a06c
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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