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Methyl Isocyanate → 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxy-7alpha-(N-methylcarbamoyloxy)pregn-5-en-3beta-yl acetate

HRID 1196321
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Reaktionsgleichung

Reaktionsgleichung von HRID 1196321
[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][C@@H:9]([OH:35])[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2[O:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][O:18]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].[CH3:36][N:37]=[C:38]=[O:39].C(OCC)(=O)C.CCCCCC>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][C@@H:9]([O:35][C:38](=[O:39])[NH:37][CH3:36])[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2[O:18][CH2:19][C:20]([CH3:23])([CH3:24])[CH2:21][O:22]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]
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Komponenten

6

Edukt 3

HCID 12228Methyl IsocyanateHCID 21226206Ethyl acetate hexaneHCID 8674580220-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxy-7alpha-hydroxypregna-5-en-3beta-yl acetate

Produkt 1

HCID 8846371220-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxy-7alpha-(N-methylcarbamoyloxy)pregn-5-en-3beta-yl acetateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In 5 ml of toluene was dissolved 49.0 mg (0.1 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxy-7α-hydroxypregn-5-en-3β-yl acetate, followed by addition of one drop of pyridine. Then, 0.1 ml (1.7 mmoles) of methyl isocyanate was added at a temperature of 0° C. and the mixture was stirred at a temperature of 60° C. for 30 minutes. The reaction mixture thus obtained was cooled to room temperature, poured in ice-water, and extracted 3 times with 20 ml portions of methylene chloride. The extracts are pooled, washed successively with water and aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. Finally the residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1:10, v/v) to recover 35 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxy-7α-(N-methylcarbamoyloxy)pregn-5-en-3β-yl acetate (yield: 65%).

Aufarbeitung

  1. customThe reaction mixture thus obtained
  2. temperaturewas cooled to room temperature
  3. extractionextracted 3 times with 20 ml portions of methylene chloride
  4. washwashed successively with water and aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customFinally the residue was purified by silica gel chromatography (eluent

Quellen und Nachweise

ORD-Eintrag
ord-394d19debeef442380d961d8c53d8423
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05112998

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