Dichloromethane → Calcitriol

HRID 2259557

Reaktionsgleichung

Reaktionsgleichung von HRID 2259557
CCN(C1C=CC2C3(C4C(OC=2C=1)=CC(C)=C(NC1C=CC=CC=1)C=4)OC(=[O:20])C1C3=CC=CC=1)CC.C(O)[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO.[CH3:114][C@@H:115]([C@@H:122]1[C@@:126]2([CH3:142])[CH2:127][CH2:128][CH2:129]/[C:130](=[CH:131]\[CH:132]=[C:133]3\[CH2:134][C@@H:135]([OH:141])[CH2:136][C@H:137]([OH:140])[C:138]\3=[CH2:139])/[C@@H:125]2[CH2:124][CH2:123]1)[CH2:116][CH2:117][CH2:118][CH:119]([CH3:121])[CH3:120].C(Cl)Cl>C(O)C>[CH3:114][C@@H:115]([C@@H:122]1[C@@:126]2([CH3:142])[CH2:127][CH2:128][CH2:129]/[C:130](=[CH:131]\[CH:132]=[C:133]3\[CH2:134][C@@H:135]([OH:141])[CH2:136][C@H:137]([OH:140])[C:138]\3=[CH2:139])/[C@@H:125]2[CH2:124][CH2:123]1)[CH2:116][CH2:117][CH2:118][C:119]([OH:20])([CH3:120])[CH3:121]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 1224022-Anilino-3-methyl-6-diethylaminofluoranHCID 444041beta-Cyclodextrin2×HCID 5282181Alfacalcidol2×

Produkt 1

HCID 5280453Calcitriol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Nocardia autotrophica N-102 in the same BG medium (100 ml/500 ml-Erlenmeyer flask) as used in Example 1 was cultured at 28° C. under the aerobic conditions for 48 hours. To the culture medium were added 10 ml of a 5% aqueous β-cyclodextrin solution (0.01 M phosphate buffer, pH 7.0), a solution of 1% 1-hydroxyvitamin D3 in 1 ml of ethanol (in the amount of 140 mol of β-cyclodextrin relative to 1 mol of 1α-hydroxyvitamin D3) and a solution of 20% Tween 80 in 1 ml of ethanol. After cultivation for a further 2 hours, methylene chloride was added to the flask, and the determination as described in Example 1 was carried out. The peak fraction having a retention time of 3.8 minutes was collected, concentrated to dryness at 40° C. or below under reduced pressure, and applied to HPLC on Zorbax ODS (made by Du Pont Co.) with water-methanol (1:9) as a mobile phase at a flow rate of 1.0 ml/min. After elution, the peak reaction having a retention time of 5.6 minutes was collected, and concentrated to dryness under pressure at 40° C. or below with a nitrogen gas replacement to give 645 μg (64.5% of conversion ratio from the material) of 1α,25-dihydroxyvitamin D3. In case of the same procedure as described above but without β-cyclodextrin, the yield was 350 μg (35% of the conversion ratio from the material).

Aufarbeitung

  1. waitAfter cultivation for a further 2 hours
  2. customwas collected
  3. concentrationconcentrated to dryness at 40° C. or below under reduced pressure
  4. washAfter elution
  5. customthe peak reaction
  6. customwas collected
  7. concentrationconcentrated to dryness under pressure at 40° C. or below with a nitrogen gas replacement

Quellen und Nachweise

ORD-Eintrag
ord-206bafe1ef3c4cff95dc27606e90b664
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05474923

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