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Water → (20S)-4-amino-21-hydroxy-20-methylpregna-4,6-dien-3-one benzoate

HRID 2082415
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2082415
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1[C:12]23[C@:28]([CH3:33])([CH2:29][CH2:30][C:31](=[O:32])[CH:11]12)[C@@H:27]1[C@H:15]([C@H:16]2[C@:24]([CH3:34])([CH2:25][CH2:26]1)[C@@H:19]([C@H:20]([CH3:23])[CH2:21][OH:22])[CH2:18][CH2:17]2)[CH2:14][CH2:13]3.[N-:35]=[N+]=[N-].[Na+].S(=O)(=O)(O)O.O>CS(C)=O>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:35][C:11]1[C:31](=[O:32])[CH2:30][CH2:29][C@@:28]2([CH3:33])[C:12]=1[CH:13]=[CH:14][C@@H:15]1[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:34])[C@H:16]1[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:23])[CH2:21][OH:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 86745921(20S)-4,5-epoxy-21-hydroxy-20-methylpregnan-3-one benzoate

Produkt 1

HCID 67744905(20S)-4-amino-21-hydroxy-20-methylpregna-4,6-dien-3-one benzoateAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a vigorously stirred solution of (20S)-4,5-epoxy-21-hydroxy-20-methylpregnan-3-one benzoate (1.0 g, 2.22 mmole) in dimethyl sulfoxide (35 mL), heated to 60° C, there was added sodium azide (2.7 g) and the concentrated sulfuric acid (0.2 mL). The mixture was quickly brought to a temperature of 100° C. and held at that temperature for 1 hour. The cooled mixture was then poured onto cold water (250 mL). The resulting mixture was extracted with ether (300 mL) and the ether solution was washed with brine, dried over magnesium sulfate and filtrate and the filtrate was concentrated to give a yellow solid which was purified by chromatography to give (20S)-4-amino-21-hydroxy-20-methylpregna-4,6-dien-3-one benzoate (0.8 g, 80.1%) melting at 163°-167° C. with decomposition. IR 3470, 3366, 1718, 1682 (m), 1656, 1608 (m), 1586 (m), 1567 (m), 1274, 1268, 718 cm-1 ; MS (CI) 448 (100%, M+1), 326 (35%, M+1-PhCOOH); 1H NMR (CDCl3) δ0.82 (3H, s, C18 -Me), 1.07 (s, C19 -Me), 1.15 (d, C22 -Me), 3.71 (2H, v br, NH2), 4.07 (1H, dd, 1/2C21 -CH2), 4.35 (1H, dd, 1/2C21 -CH2), 5.98 (1H dd), 6.30 (1H dd), 7.35 (2H, t), 7.57 (1H, t), 8.04 (2H, dd).

Aufarbeitung

  1. customwas quickly brought to a temperature of 100° C.
  2. extractionThe resulting mixture was extracted with ether (300 mL)
  3. washthe ether solution was washed with brine
  4. dry with materialdried over magnesium sulfate and filtrate
  5. concentrationthe filtrate was concentrated
  6. customto give a yellow solid which
  7. customwas purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3464253b931d4fd48e6980b0b8d39c39
Quelldatensatz
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05189032

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