p-Toluenesulfonic acid monohydrate → HCID 13189275, compound

HRID 434516Notes

Reaction equation

HRID 434516 reaction equation
O1CCCCC1[O:7][C@@H:8]1[C@@:40]2([CH3:41])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:39]2[CH2:38][CH2:37][C@@:36]2([CH3:42])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:35])[CH2:21][CH2:22][C:23]([F:34])([F:33])[C:24]([O:27]C(OCC)C)([CH3:26])[CH3:25])[CH2:11][C@@H:10]([O:43]C2CCCCO2)[CH2:9]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[F:33][C:23]([F:34])([CH2:22][CH2:21][C@H:20]([C@@H:19]1[C@:36]2([CH3:42])[C@H:16]([C@H:15]3[C@H:39]([CH2:38][CH2:37]2)[C@:40]2([CH3:41])[C:12]([CH2:11][C@@H:10]([OH:43])[CH2:9][C@@H:8]2[OH:7])=[CH:13][CH2:14]3)[CH2:17][CH2:18]1)[CH3:35])[C:24]([OH:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 13189273HCID 13189273, compound

Product 1

HCID 13189275HCID 13189275, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1.87 g (0.0027 mol) of [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-ene, 70 mL of methanol and 0.30 g of p-toluenesulfonic acid monohydrate was stirred at 25° C. for 4 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]-24,24-difluorocholest-5-en-1,3,25-triol, mp 177°-179°, [α]D21 -15° (c 0.6, MeOH).

Workup

  1. customThe mixture was quenched
  2. additionby adding 1.0 g of sodium bicarbonate
  3. stirringstirring for 0.5 hr
  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-65e806b6879647eba6b7f7b61f018f84
Source dataset
uspto-grants-1983_08
Patent number
US04397847

Reaction notes

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