Potassium Bicarbonate → HCID 22810352, compound

HRID 1701435Notes

Reaction equation

HRID 1701435 reaction equation
C([O:4][CH2:5][C:6](=[O:38])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C@@H:22]([O:26][C:27](=[O:36])[CH2:28][N:29]([CH2:33][CH2:34][CH3:35])[CH2:30][CH2:31][CH3:32])[CH2:23]2)[C@:19]2([CH3:20])[C@H:14]([CH2:15][C@H:16]([OH:37])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)(=O)C.C(=O)([O-])O.[K+]>CO>[OH:37][C@@H:16]1[CH2:17][CH2:18][C@@:19]2([CH3:20])[C@@H:14]([CH2:13][CH2:12][C@@H:11]3[C@@H:21]2[C@@H:22]([O:26][C:27](=[O:36])[CH2:28][N:29]([CH2:33][CH2:34][CH3:35])[CH2:30][CH2:31][CH3:32])[CH2:23][C@@:24]2([CH3:25])[C@H:10]3[CH2:9][CH2:8][C@@H:7]2[C:6](=[O:38])[CH2:5][OH:4])[CH2:15]1

Participants

4

Reactant 2

HCID 516893Potassium BicarbonateHCID 22810341HCID 22810341, compound

Product 1

HCID 22810352HCID 22810352, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21-Acetoxy-11β-N,N-dipropylaminoacetoxy-3α-hydroxy-5α-pregnan-20-one (800 mg) in methanol (16 ml) was refluxed with 20% aqueous potassium hydrogen carbonate solution (4 ml) under nitrogen for 1 hour. The mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed, dried and evaporated. The residue was purified by preparative TLC (ethyl acetate-petroleum ether b.p. 40°-60° (2:1)×2) and triturated with pentane to give title compound (219 mg) m.p. 98°-102°, [α]D +66°.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried
  4. customevaporated
  5. customThe residue was purified by preparative TLC (ethyl acetate-petroleum ether b.p. 40°-60° (2:1)×2)
  6. customtriturated with pentane

Sources & evidence

ORD record
ord-419dcbfb77df42e6bcb6509bb5c63a7c
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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