Benzoyl chloride → (20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate

HRID 893039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 893039
[OH:1][CH2:2][C@@H:3]([CH3:24])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:32]([OH:39])(=[O:1])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[OH:1][CH2:2][C@@H:3]([CH3:24])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11142115HCID 11142115, Verbindung

Produkt 1

HCID 86745920(20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoateAusbeute 171,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of (20S)-21-hydroxy-20-methylpregn-4-en-3-one (8.0 g, 24.2 mmole) in dichloromethane (200 mL) was cooled in an ice-water bath and treated sequentially with triethylamine (3.69 mL, 26.6 mmole) and benzoyl chloride (3.09 mL, 26.6 mmole) and stirred for 16 hours at room temperature. After the reaction mixture was diluted with dichloromethane (200 mL), it was extracted with ether, dried over magnesium sulfate and filtered and the filtrate was concentrated to a solid which was purified by flash chromatography to give (20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate (9.4 g, 89.5%) melting at 193°-195° C. after recrystallization from acetone. IR 1716, 1676, 1614 (m), 1284 cm-1 ; MS (CI) 435 (100%, M+1), 313 (70%, M+1-PhCOOH); 1H NMR (CDCl3) δ 0.77 (3H, s, C18 -Me), 1.04 (d, C22 -Me), 1.19 (s, C19 -Me), 4.05 (1H, dd, 1/2 C2 -CH2), 4.34 (1H, dd, 1/2 C21 -CH2), 5.72 (1H, s, C4 -H), 7.45 (2H, t), 7.56 (1H, t), 8.04 (2H, dd).

Aufarbeitung

  1. extractionwas extracted with ether
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to a solid which
  5. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a017275f2f344893a136dd5c99de3930
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05120840

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