Betamethasone Valerate → (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11beta,21-dihydroxy-3,20-dioxo-9-fluoro-16beta-methyl-17-valeroyloxy-pregna-1,4-dien-21-yl] ester

HRID 53069

Reaktionsgleichung

Reaktionsgleichung von HRID 53069
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][C@@:8]1([C:31]([CH2:33][OH:34])=[O:32])[C@@:12]2([CH3:29])[CH2:13][C@H:14]([OH:28])[C@:15]3([F:27])[C@:25]4([CH3:26])[C:19](=[CH:20][C:21]([CH:23]=[CH:24]4)=[O:22])[CH2:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][C@@H:9]1[CH3:30])=[O:6].[C:35]([NH:42][C@H:43]([C:47]([OH:49])=[O:48])[CH:44]([CH3:46])[CH3:45])([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].C(OCC)(=O)C.CCCCCC>CN(C)C1C=CN=CC=1.ClCCl.O1CCOCC1>[OH:28][C@H:14]1[CH2:13][C@@:12]2([CH3:29])[C@@H:11]([CH2:10][C@H:9]([CH3:30])[C@:8]2([O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][CH3:1])[C:31](=[O:32])[CH:33]([O:49][C:47](=[O:48])[C@@H:43]([NH:42][C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36])[CH:44]([CH3:45])[CH3:46])[OH:34])[C@H:16]2[C@@:15]1([F:27])[C@:25]1([CH3:26])[C:19]([CH2:18][CH2:17]2)=[CH:20][C:21](=[O:22])[CH:23]=[CH:24]1

Komponenten

6

Edukt 3

HCID 16533Betamethasone ValerateHCID 83693Boc-L-ValineHCID 21226206Ethyl acetate hexane2×

Produkt 1

HCID 131719966(2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11beta,21-dihydroxy-3,20-dioxo-9-fluoro-16beta-methyl-17-valeroyloxy-pregna-1,4-dien-21-yl] esterAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 18626912Dioxane methylene chlorideLösungsmittel

Versuchsvorschrift

21 mmol of betamethasone-17-valerate is reacted with 25 mmol of Boc-valine (Boc-Val-OH), 2.5 mmol of 4-dimethylaminopyridine and 27 mmol of dicyclohexylcarbodiimidazole in dichloromethane/dioxane 1:1 analogously to Example 1. Chromatography (1. ethyl acetate/hexane 2:1 and 2. ethyl acetate/hexane 1:1) yields 10.1 g (73%) of pure (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11β,21-dihydroxy-3,20-dioxo-9-fluoro-16β-methyl-17-valeroyloxy-pregna -1,4-dien-21-yl] ester as foam.

Quellen und Nachweise

ORD-Eintrag
ord-4aa3a2e7e4c1420a8ea5ecf484c50303
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616573

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