Acetic Anhydride → HCID 86734305, compound

HRID 1973734Notes

Reaction equation

HRID 1973734 reaction equation
OCC[C:4](=[O:32])[C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([C:20](=[O:24])[CH2:21]2)[C@:17]2([CH3:18])[C@H:12]([CH2:13][C@H:14]([O:25]C4CCCCO4)[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1.[C:33]([O:36][C:37](=[O:39])[CH3:38])(=O)[CH3:34]>N1C=CC=CC=1>[C:37]([O:36][CH2:33][CH2:34][C:4](=[O:32])[C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([C:20](=[O:24])[CH2:21]2)[C@:17]2([CH3:18])[C@H:12]([CH2:13][C@H:14]([OH:25])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1)(=[O:39])[CH3:38]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86734306HCID 86734306, compound

Product 1

HCID 86734305HCID 86734305, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

21Hydroxymethyl-3α-tetrahydropyranyloxy-5α-pregnane-11,20- dione (600 mg) in anhydrous pyridine (12 ml) was treated with acetic anhydride (1.0 ml), and the solution was stirred at room temperature for 21/2 hours. The solution was partitioned between hydrochloric acid (2N, 100 ml) and ether/ethyl acetate 1/1, and the organic phase was washed with water, dried over sodium sulphate and evaporated to an oil (640 mg). The crude product (630 mg) was dissolved in I.M.S. (25 ml) and dilute hydrochloric acid (2N; 2.5 ml) was added. The solution was stirred at room temperature for 2 hours. The solution was neutralised with 10% potassium bicarbonate solution (5 ml) and concentrated by evaporation until an oily solid began to separate. The mixture was then diluted with water and extracted twice with ether/ethyl acetate 1/1. The combined organic extract was washed with water, dried over sodium sulphate and evaporated to a pale yellow oil (500 mg) which as purified by preparative t.l.c. in ethyl acetate/petrol 1/1. The main band, Rf 0.3 was separated to give 242 mg of solid which was recrystallized from ethyl acetate/petrol to give title compound (187 mg) as colourless plates, m.p. 113°-115°, [α]D + 103° (c 1.32).

Workup

  1. customThe solution was partitioned between hydrochloric acid (2N, 100 ml) and ether/ethyl acetate 1/1
  2. washthe organic phase was washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to an oil (640 mg)
  5. dissolutionThe crude product (630 mg) was dissolved in I.M.S
  6. addition(25 ml) and dilute hydrochloric acid (2N; 2.5 ml) was added
  7. stirringThe solution was stirred at room temperature for 2 hours
  8. concentrationconcentrated by evaporation until an oily solid
  9. customto separate
  10. additionThe mixture was then diluted with water
  11. extractionextracted twice with ether/ethyl acetate 1/1
  12. extractionThe combined organic extract
  13. washwas washed with water
  14. dry with materialdried over sodium sulphate
  15. customevaporated to a pale yellow oil (500 mg) which
  16. customas purified by preparative t.l.c
  17. customThe main band, Rf 0.3 was separated

Sources & evidence

ORD record
ord-308f875de8924c89a220dae4f5ea0bff
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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