Chlorosulfamic acid → Estrone sulfamate

HRID 1831859Notes

Reaction equation

[S:1](=[O:24])(=[O:23])([O:3][C:4]1[CH:21]=[CH:20][C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C@@H:13]([OH:22])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=1)[NH2:2].S(Cl)(=O)(=O)N>>[S:1](=[O:23])(=[O:24])([O:3][C:4]1[CH:21]=[CH:20][C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13](=[O:22])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=1)[NH2:2]

Participants

Reactant 2

HCID 24499Chlorosulfamic acid

HCID 6918339Estradiol sulfamate

Product 1

HCID 127676Estrone sulfamate

Procedure

Sulfamoylation is the key step in the synthesis of 17β-Hydroxyestra-1,3,5(10)-trien-3-yl sulfamate, a potent estrogen after oral administration. 17-Oxo-1,3,5(10)-triene-3-ol (estrone) is reacted with sulfamoyl chloride to yield 17-Oxoestra-1,3,5(10)-trien-3-yl sulfamate, which is in turn converted to 17β-Hydroxyestra-1,3,5(10)-trien-3-yl sulfamate by means of a complex hydride reagent. According to this invention, the preferred complex hydride reagent is sodium borohydride.

Sources & evidence

ORD record: ord-192691e0c66446ba99dea9eb3a5fb85d
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067683B2

Reaction notes

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