19-Hydroxypregn-4-ene-3,20-dione → HCID 14695953, compound

HRID 1165453Notes

Reaction equation

[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:24])[CH2:9][CH2:10][C@@H:11]3[C@:21]4([CH2:22]O)[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].CCOC([S-])=[S:29].[K+]>>[SH:29][CH2:22][C@@:21]12[C@@H:11]3[C@H:12]([C@H:7]4[C@:8]([CH3:24])([CH2:9][CH2:10]3)[C@@H:4]([C:2](=[O:3])[CH3:1])[CH2:5][CH2:6]4)[CH2:13][CH2:14][C:15]1=[CH:16][C:17](=[O:18])[CH2:19][CH2:20]2

Participants

Reactant 2

HCID 15078219-Hydroxypregn-4-ene-3,20-dione

HCID 2735045Potassium ethylxanthate

Product 1

HCID 14695953HCID 14695953, compound

Procedure

19-Hydroxyprogesterone is converted to the trifluoromethanesulfonate ester, the sulfonate is displaced with potassium ethyl xanthogenate and the resulting steroid xanthogenate is hydrolyzed to give 19-mercaptopregn-4-ene-3,20-dione, all according to the procedure described by P. J. Bednarski, D. J. Porubek and S. D. Nelson, J. Med. Chem., 28, 775-779 (1985).

Sources & evidence

ORD record: ord-ffd0f2dde59c410b8bd599f2ebbc8be5
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04910191

Reaction notes

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