Water → HCID 10673665, compound

HRID 233508Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C@@H:7]1[C@@H:27]([N:28]2[CH2:33][CH2:32][O:31][C:30]([CH3:35])([CH3:34])[CH2:29]2)[CH2:26][C@@:25]2([CH3:36])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:37])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:20])[CH2:18][OH:19])[CH2:8]1.O.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[OH:6][C@@H:7]1[C@@H:27]([N:28]2[CH2:33][CH2:32][O:31][C:30]([CH3:35])([CH3:34])[CH2:29]2)[CH2:26][C@@:25]2([CH3:36])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:37])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:20])[CH2:18][O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:8]1

Participants

Conditions

Temperature: -25 °C

Procedure

A solution of methanesulfonyl chloride (2.48 ml) in dry pyridine (9.6 ml) was added to a solution of the 3,21-dihydroxy compound of Example 9 (3.26 g) in dry pyridine (33 ml) at -25° C. over ca. 5 min. The solution was stirred at -25° C. for 1.5 h and poured into water (400 ml). Aqueous sodium carbonate was added until the pH exceeded 9 and the precipitated solid was filtered off and dissolved in dichloromethane. The solution was dried over sodium sulfate and the solvent was removed under reduced pressure to give (2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-[(methylsulfonyl)oxy]pregnan-20-one (3.80 g). δ (CDCl3) 0.65 (s,3H), 0.86 (s,3H), 3.22 (s,3H) and 4.79 (m,2H).

Workup

filtrationthe precipitated solid was filtered off
dissolutiondissolved in dichloromethane
dry with materialThe solution was dried over sodium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-7605d7b20a6c402d803718d3be41ffed
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05593983

Reaction notes

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