Fluocortolone → (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11beta,21-dihydroxy-6alpha-fluoro-16alpha-methyl-3,20-dioxo-pregna-1,4-dien-21-yl] ester

HRID 53067

Reaktionsgleichung

Reaktionsgleichung von HRID 53067
[CH3:1][C@H:2]1[C@H:19]([C:20]([CH2:22][OH:23])=[O:21])[C@:18]2([CH3:24])[C@H:4]([C@H:5]3[C@H:15]([C@@H:16]([OH:25])[CH2:17]2)[C@:14]2([CH3:26])[C:8](=[CH:9][C:10]([CH:12]=[CH:13]2)=[O:11])[C@@H:7]([F:27])[CH2:6]3)[CH2:3]1.[C:28]([NH:35][C@H:36]([C:40]([OH:42])=[O:41])[CH:37]([CH3:39])[CH3:38])([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C1(N=C=NC2CCCCC2)CCCCC1.C(OCC)(=O)C.CCCCCC>CN(C)C1C=CN=CC=1.ClCCl.O1CCOCC1>[OH:25][C@H:16]1[CH2:17][C@@:18]2([CH3:24])[C@@H:4]([CH2:3][C@@H:2]([CH3:1])[C@@H:19]2[C:20](=[O:21])[CH:22]([O:42][C:40](=[O:41])[C@@H:36]([NH:35][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH:37]([CH3:38])[CH3:39])[OH:23])[C@H:5]2[C@H:15]1[C@:14]1([CH3:26])[C:8]([C@@H:7]([F:27])[CH2:6]2)=[CH:9][C:10](=[O:11])[CH:12]=[CH:13]1

Komponenten

7

Edukt 4

HCID 9053FluocortoloneHCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-ValineHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 131719962(2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11beta,21-dihydroxy-6alpha-fluoro-16alpha-methyl-3,20-dioxo-pregna-1,4-dien-21-yl] esterAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 18626912Dioxane methylene chlorideLösungsmittel

Versuchsvorschrift

26 mmol of fluocortolone (FC) is reacted with 32 mmol of Boc-valine (Boc-Val-OH), 2.9 mmol of 4-dimethylaminopyridine and 34 mmol of dicyclohexylcarbodiimide in dichloromethane/dioxane 3:2. Chromatography (ethyl acetate/hexane 2:1): F1 9.3 g of pure product, F2 4.8 g of slightly contaminated product. (Total yield 92%) crystallization of F1 from ethyl acetate/hexane yields 7.0 g (46%) of (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11β,21-dihydroxy-6α-fluoro-16α-methyl-3,20-dioxo-pregna-1,4-dien-21-yl] ester.

Aufarbeitung

  1. custom(Total yield 92%) crystallization of F1 from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-6c63a7b0bcdf4386a1182731aa9a9a7e
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616573

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