Hydrochloric Acid → HCID 386752, compound

HRID 2121348Notes

Reaction equation

HRID 2121348 reaction equation
[OH-].[K+].C([O:6][C:7]1[C:24]([O:25][CH2:26][CH3:27])=[CH:23][C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([O:28]C(=O)C)[CH2:15][CH2:14]4)[CH2:11][C:10](=[O:32])[C:9]=2[CH:8]=1)(=O)C.Cl>CO>[OH:6][C:7]1[C:24]([O:25][CH2:26][CH3:27])=[CH:23][C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([OH:28])[CH2:15][CH2:14]4)[CH2:11][C:10](=[O:32])[C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 11796064HCID 11796064, compound

Product 1

HCID 386752HCID 386752, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under nitrogen, a 20% solution of potassium hydroxide in methanol (15 ml) was added dropwise at room temperature to a suspension of compound 5 (3.0 g, 7.26 mmol) in anhydrous methanol (60 ml). The resulting mixture was stirred at room temperature for 6 hr. The mixture was neutralized with 3 N HCl and the solvent was removed under reduced pressure. The residue was diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layer was washed with brine (2×100 ml), and dried over sodium sulfate. Removal of the solvents provided a white solid 6 (2.34 g, 98%), which was then crystallized from ethyl acetate/hexane to afford title compound 6 as white crystals: mp 197-199° C. (lit. 12 mp 194-196° C.); 1H NMR (CDCl3) δ7.61 (s, 1 H, 4-aromatic CH), 7.20 (s, 1 H, 1-aromatic CH), 4.44 (q, J=6.9 Hz, 2 H, 2-CH2-), 3.83 (t, J=8.5 Hz, 1 H, 17α-H), 2.85-1.40 (m, 20H), 0.97 (s, 3 H, 18-CH3).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water (100 ml)
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined organic layer was washed with brine (2×100 ml)
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvents

Sources & evidence

ORD record
ord-551a85e37ae8481c8e47aa4502bde812
Source dataset
uspto-grants-2004_02
Patent number
US06696436B1

Reaction notes

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