Methanesulfonyl chloride → HCID 86733251, compound

HRID 1606298Notes

Reaction equation

HRID 1606298 reaction equation
[OH:1][C:2]1[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:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[S:23]([O:1][C:2]1[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:20])[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:21][S:23]([CH3:22])(=[O:25])=[O:24])[CH:3]=1)([CH3:22])(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68148298HCID 68148298, compound

Product 1

HCID 86733251HCID 86733251, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1 g. of 1,3-dihydroxy-8α-estra-1,3,5(10)-trien-17-one (prepared from compound of Example 9 by saponification) in 14 ml. of pyridine is combined at 0° C. with 1.9 ml. of methanesulfonic acid chloride and agitated for 3 days at 0°-10° C. The mixture is then introduced into ice water (acidified with HCl), filtered off, and the residue dissolved in methylene chloride. After chromatography on SiO2, 800 mg. of 1,3-bis(mesyloxy)-8α-estra-1,3,5(10)-trien-17-one is obtained.

Workup

  1. customis combined at 0° C. with 1.9 ml
  2. filtrationfiltered off
  3. dissolutionthe residue dissolved in methylene chloride

Sources & evidence

ORD record
ord-c4532130e6f042d9afdef0439fbea9f4
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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