p-Toluenesulfonic acid monohydrate → HCID 13826519, compound

HRID 1906689Notes

Reaction equation

HRID 1906689 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 13826517HCID 13826517, compound

Product 1

HCID 13826519HCID 13826519, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.56 g. (0.0053 mole) of [1α,3β,24R]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-ene, 140 ml. of methanol and 0.58 g. of p-toluenesulfonic acid monohydrate was stirred at 25° C. for 3 hr. The mixture was quenched by adding 1.0 g. of sodium bicarbonate and stirring for 0.5 hr. The mixture was then evaporated to dryness. The residue was triturated with ethyl acetate, filtered, and evaporated to dryness. The crude solid was recrystallized from ethyl acetate to yield [1α,3β,24R]-24-fluorocholest-5-en-1,3,25-triol, mp 156°-158°, [α]D21 +4° (c 0.5, MeOH).

Workup

  1. additionA mixture of 3.56 g
  2. customThe mixture was quenched
  3. additionby adding 1.0 g
  4. customThe mixture was then evaporated to dryness
  5. customThe residue was triturated with ethyl acetate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b80675a80f564a61b3f301b7e018d28e
Source dataset
uspto-grants-1987_03
Patent number
US04652405

Reaction notes

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