Water → HCID 86748786, compound

HRID 233650Notes

Reaction equation

HRID 233650 reaction equation
[OH:1][CH:2]([CH2:33][OH:34])[CH2:3][O:4][CH2:5][CH2:6][O:7][C@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@:14]3([OH:32])[CH2:15][CH2:16][C@@H:17]2[C:27]2[CH:31]=[CH:30][O:29][CH:28]=2)[CH2:9]1.[S:35](Cl)([C:38]1[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=1)(=[O:37])=[O:36].O.C(OCC)(=O)C>N1C=CC=CC=1>[S:35]([O:34][CH2:33][CH:2]([OH:1])[CH2:3][O:4][CH2:5][CH2:6][O:7][C@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@:14]3([OH:32])[CH2:15][CH2:16][C@@H:17]2[C:27]2[CH:31]=[CH:30][O:29][CH:28]=2)[CH2:9]1)([C:38]1[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=1)(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 70044593HCID 70044593, compound

Product 1

HCID 86748786HCID 86748786, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.7 g of 3β-(2-(2,3-dihydroxypropoxy)ethoxy)-17β-(3-furyl)-5β-androstan-14β-ol, prepared from 3β-(2-hydroxyethoxy)-17β-(3-furyl)-5β-andostran-14β-ol, prepared as an intermediate in Ex.1, according to the sequence described in Ex. 2 and Ex. 15, in 13 ml of dry pyridine, 0.80 g of tosyl chloride were added at a temperature of 0° C. After 5 hrs 60 ml of water and 250 ml of ethyl acetate were added, the organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2)using n-hexane/ethyl acetate 70/30 as eluant to give 2 g of 3β-(2-(3-tosyloxy-2-hydroxypropoxy)ethoxy)-17β-(3-furyl)-5β-androstan-14β-ol as a white solid.

Workup

  1. customprepared as an intermediate in Ex.1
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe crude product was purified by flash-chromatography (SiO2)using n-hexane/ethyl acetate 70/30 as eluant

Sources & evidence

ORD record
ord-9eb6339194b14f88be37d9307f15d83b
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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