Benzenesulfinic acid, sodium salt → 1alpha,3beta-Bis(methoxycarbonyloxy)-20-methyl-21-phenylsulfonylpregna-5,7-diene

HRID 1587634Notes

Reaction equation

I[CH2:2][CH:3]([CH3:33])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11]([CH2:12][C@@H:13]([O:28][C:29]([O:31][CH3:32])=[O:30])[CH2:14][C@@H:15]2[O:23][C:24]([O:26][CH3:27])=[O:25])=[CH:10][CH:9]=3)[CH2:6][CH2:5]1.[C:34]1([S:40]([O-:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Na+]>CN(C)C=O>[CH3:33][CH:3]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11]([CH2:12][C@@H:13]([O:28][C:29]([O:31][CH3:32])=[O:30])[CH2:14][C@@H:15]2[O:23][C:24]([O:26][CH3:27])=[O:25])=[CH:10][CH:9]=3)[CH2:6][CH2:5]1)[CH2:2][S:40]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:42])=[O:41]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 71 mg of 21-iodo-20-methyl-1α,3β-bis-(methoxycarbonyloxy)pregna-5,7-diene, 80 mg of sodium benzenesulfinate and 3 ml of dimethylformamide was stirred at 40° C. for 7 hours. The reaction mixture was subjected to the same isolation and purification procedure in Example 5 to give 42 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-phenylsulfonylpregna-5,7-diene, whose 1H NMR spectrum was identical with that obtained in Example 5.

Workup

customThe reaction mixture was subjected to the same isolation and purification procedure in Example 5

Sources & evidence

ORD record: ord-4c3bd46928f34d3eaacf276ac149a06c
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05218109

Reaction notes

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