(2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)-11,20-dioxopregnane-21-carbonitrile → (2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-thiocyanatopregnan-20-one methanesulfonate

HRID 233524Notes

Reaction equation

HRID 233524 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C@@H:7]1[C@@H:28]([N:29]2[CH2:34][CH2:33][O:32][C:31]([CH3:36])([CH3:35])[CH2:30]2)[CH2:27][C@@:26]2([CH3:37])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:25]2[C:24](=O)[CH2:23][C@@:22]2([CH3:39])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:21])[CH2:18]C#N)[CH2:8]1.O[C@@H]1[C@@H]([N:63]2[CH2:68]COC(C)(C)C2)C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2C(=O)C[C@@]2(C)[C@H]3CC[C@@H]2C(=O)CC#N)C1>>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C@@H:7]1[C@@H:28]([N:29]2[CH2:34][CH2:33][O:32][C:31]([CH3:36])([CH3:35])[CH2:30]2)[CH2:27][C@@:26]2([CH3:37])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:39])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:21])[CH2:18][S:2][C:68]#[N:63])[CH2:8]1

Participants

3

Reactant 2

HCID 53955604(2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)-11,20-dioxopregnane-21-carbonitrileHCID 88359612(2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)-11,20-dioxopregnane-21-carbonitrile methanesulfonate

Product 1

HCID 86750182(2beta,3alpha,5alpha)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-thiocyanatopregnan-20-one methanesulfonate

Procedure

(2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)-11,20-dioxopregnane-21-carbonitrile methanesulfonate (1:1) salt with the 21-cyano compound of Example 37 as starting material. δ (CDCl3) 0.66 (s,3H), 1.09 (s,3H), 1.34 (s,3H), 1.52 (s,3H), 2.81 (s,3H), 3.42 (s,2H) and 4.27 (t,J 13 Hz, 1H).

Sources & evidence

ORD record
ord-55d1773acdc745e9881fb361ee926cbd
Source dataset
uspto-grants-1997_01
Patent number
US05593983

Reaction notes

Loading…