Methanesulfonyl chloride → HCID 86733256, compound

HRID 1606275Notes

Reaction equation

HRID 1606275 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])[C@H:12]([OH:21])[CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([OH:22])[CH:3]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[S:24]([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])[C@H:12]([O:21][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([O:22][S:24]([CH3:23])(=[O:26])=[O:25])[CH:3]=1)([CH3:23])(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68147310HCID 68147310, compound

Product 1

HCID 86733256HCID 86733256, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 400 mg. of 1,3,16α-trihydroxy-8α-estra-1,3,5(10)-trien-17-one in 5 ml. of pyridine is combined at 0° C. with 1.5 ml. of methanesulfonic acid chloride and agitated for 3 days at 0°-10° C. The mixture is thereafter introduced inyo ice water (acidified with HCl), filtered off, and the residue is dissolved in methylene chloride. After chromatography on SiO2, 250 mg. of 1,3,16α-tris(mesyloxy)-8α-estra-1,3,5(10)-trien-17-one is obtained.

Workup

  1. customis combined at 0° C. with 1.5 ml
  2. filtrationfiltered off
  3. dissolutionthe residue is dissolved in methylene chloride

Sources & evidence

ORD record
ord-5224fbbc555f44a5b4e7e1e14b5806bd
Source dataset
uspto-grants-1976_04
Patent number
US03951958

Reaction notes

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