Sodium Hydroxide → 25-Hydroxy-7-dehydrocholesterol

HRID 741544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 741544
[OH:1][C@@:2]1(CC([O-])=O)[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:4](=[CH:5][CH:6]=[C:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[CH2:3]1.[OH-].[Na+]>C(O)C>[OH:1][C@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:4](=[CH:5][CH:6]=[C:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([OH:19])([CH3:17])[CH3:18])[CH2:3]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 867497783beta,25-Dihydroxycholesta-5,7-diene-3-acetate

Produkt 1

HCID 990898325-Hydroxy-7-dehydrocholesterolAusbeute 112,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of acetate 9a (75 mg) in ethanol (10 ml) containing 5% aqueous NaOH (1 ml) was set aside for 24 h and then the solvent was evaporated in vacuo. The residue was taken in ethyl acetate (30 ml) and washed consecutively with 5% HCl, water, and saturated aqueous NaHCO3. Evaporation of the solvent gave (20S) 3b,25-dihydroxycholesta-5,7-diene 9b (74 mg) which was used for the next step without purification; λmax 240, 249, 260 and 272 nm; high resolution mass spec. for C27H44O2 calcd.: 400.3341(M+); found: 400.3334(100%), 398.3162(M+ --H2O, 11%), 385.3101(M+ --CH3, 14%), 380.3086, 24%), 367.3013(M+ --CH3 --H2O, 67%).

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. washwashed consecutively with 5% HCl, water, and saturated aqueous NaHCO3
  3. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-f0bad110599e4c40a3014b4f3ec079ff
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05552392

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