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

HRID 1165450Notes

Reaction equation

HRID 1165450 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

3

Reactant 2

HCID 15078219-Hydroxypregn-4-ene-3,20-dioneHCID 2735045Potassium ethylxanthate

Product 1

HCID 14695953HCID 14695953, compound

Procedure

Other compounds can be prepared by starting with 19-hydroxyprogesterone. This is converted to the corresponding trifluoromethanesulfonate ester and the sulfonate is displaced with potassium ethyl xanthogenate. Hydrolysis of the resulting xanthogenate then gives the desired 19-mercaptopregn-4-ene-3,20-dione. This 19-mercapto compound can then be reacted with the appropriate acid halide or anhydride to give the corresponding ester.

Workup

  1. customOther compounds can be prepared
  2. customHydrolysis of the resulting xanthogenate

Sources & evidence

ORD record
ord-e9e78bb452c04474ba63bc264bf8d170
Source dataset
uspto-grants-1990_03
Patent number
US04910191

Reaction notes

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