p-Toluenesulfonic acid monohydrate → HCID 56989245, compound

HRID 980068Notes

Reaction equation

HRID 980068 reaction equation
O1CCCCC1[O:7][C@@H:8]1[C@@:39]2([CH3:40])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:38]2[CH2:37][CH2:36][C@@:35]2([CH3:41])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:34])[CH2:21][CH2:22][C@H:23]([F:33])[C:24]([O:27]C(OCC)C)([CH3:26])[CH3:25])[CH2:11][C@@H:10]([O:42]C2CCCCO2)[CH2:9]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[F:33][C@@H:23]([CH2:22][CH2:21][C@H:20]([C@@H:19]1[C@:35]2([CH3:41])[C@H:16]([C@H:15]3[C@H:38]([CH2:37][CH2:36]2)[C@:39]2([CH3:40])[C:12]([CH2:11][C@@H:10]([OH:42])[CH2:9][C@@H:8]2[OH:7])=[CH:13][CH2:14]3)[CH2:17][CH2:18]1)[CH3:34])[C:24]([OH:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57085025HCID 57085025, compound

Product 1

HCID 56989245HCID 56989245, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.356 g. (0.00053 mole) of [1α,3β,24S]-1,3-bis-[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-ene, 15 ml. of methanol and 0.05 g. of p-toluenesulfonic acid monohydrate was stirred at 25° for 3 hr. The mixture was quenched with 0.25 g. of sodium bicarbonate and stirring for 0.5 hr. The mixture was evaporated to dryness. The residue was triturated with ethyl acetate, filtered, and evaporated to dryness to yield [1α,3β,24S]-24-fluorocholest-5-en-1,3,25-triol.

Workup

  1. additionA mixture of 0.356 g
  2. customThe mixture was quenched with 0.25 g
  3. customThe mixture was evaporated to dryness
  4. customThe residue was triturated with ethyl acetate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-15be79c724f6482f9e49feff0bd2d0b9
Source dataset
uspto-grants-1987_01
Patent number
US04634692

Reaction notes

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