Methanesulfonic Acid → (2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2,6,6-tetramethyl-4-morpholinyl)pregnane-11,20-dione methanesulfonate

HRID 233514Notes

Reaction equation

HRID 233514 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C@@H:7]1[C@@H:26]([N:27]2[CH2:32][C:31]([CH3:34])([CH3:33])[O:30][C:29]([CH3:36])([CH3:35])[CH2:28]2)[CH2:25][C@@:24]2([CH3:37])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:23]2[C:22](=[O:38])[CH2:21][C@@:20]2([CH3:39])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8]1>CO>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C@@H:7]1[C@@H:26]([N:27]2[CH2:28][C:29]([CH3:36])([CH3:35])[O:30][C:31]([CH3:34])([CH3:33])[CH2:32]2)[CH2:25][C@@:24]2([CH3:37])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:23]2[C:22](=[O:38])[CH2:21][C@@:20]2([CH3:39])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:19])[CH3:18])[CH2:8]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 10719286HCID 10719286, compound

Product 1

HCID 86750175(2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2,6,6-tetramethyl-4-morpholinyl)pregnane-11,20-dione methanesulfonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of methanesulfonic acid (63 mg) in methanol (5 ml) was added to a suspension of (2β,3α,5α)-3-hydroxy-2-(2,2,6,6-tetramethyl-4-morpholinyl)pregnane-11,20-dione (311 mg) in methanol (5 ml). The solvent was removed under reduced pressure and the residue was crystallised from diethyl ether to give (2β,3α,5α)-3-hydroxy-2-(2,2,6,6-tetramethyl-4-morpholinyl)pregnane-11,20-dione methanesulfonate (1:1) salt (354 mg). m.p. 211°-217° C. (dec); [α]D +109.7° (c 0.6).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was crystallised from diethyl ether

Sources & evidence

ORD record
ord-eb1c52b310114991852e8130f3ff631f
Source dataset
uspto-grants-1997_01
Patent number
US05593983

Reaction notes

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