Methanesulfonyl chloride → HCID 86733257, compound

HRID 1606276Notes

Reaction equation

HRID 1606276 reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@H:7]([CH2:8][CH2:9][C:10]4[CH:11]=[C:12]([OH:20])[CH:13]=[C:14]([OH:19])[C:15]=43)[C@@H:6]1[CH2:5][C@@H:4]([OH:21])[C@@H:3]2[OH:22].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[S:24]([O:19][C:14]1[C:15]2[C@@H:16]3[C@@H:7]([C@H:6]4[C@@:2]([CH2:18][CH2:17]3)([CH3:1])[C@@H:3]([O:22][S:24]([CH3:23])(=[O:26])=[O:25])[C@H:4]([O:21][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:5]4)[CH2:8][CH2:9][C:10]=2[CH:11]=[C:12]([O:20][S:24]([CH3:23])(=[O:26])=[O:25])[CH:13]=1)([CH3:23])(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54441139HCID 54441139, compound

Product 1

HCID 86733257HCID 86733257, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 400 mg. of 8α-estra-1,3,5(10)-triene-1,3,16α,17β-tetrol in 5 ml. of pyridine is combined at 0° C. with 2 ml. of methanesulfonic acid chloride, and the mixture is agitated for 3 days at 0°-10° C. Thereafter, the mixture is introduced into ice water (acidified with HCl), filtered off, and the residue dissolved in methylene chloride. After purification by chromatography on SiO2, 220 mg. of rac.-1,3,16α,17β-tetrakis(mesyloxy)-8α-estra-1,3,5(10)-triene is obtained.

Workup

  1. customis combined at 0° C. with 2 ml
  2. filtrationfiltered off
  3. dissolutionthe residue dissolved in methylene chloride
  4. customAfter purification by chromatography on SiO2, 220 mg

Sources & evidence

ORD record
ord-78494f9bad5446a0a2381877d651a364
Source dataset
uspto-grants-1976_04
Patent number
US03951958

Reaction notes

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