Phenylsilane → HCID 59190389, Verbindung

HRID 219621

Reaktionsgleichung

Reaktionsgleichung von HRID 219621
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]3[CH2:23][CH2:22][CH2:21][C@:20]([CH2:30][C:31]([CH3:33])=[CH2:32])([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[NH:19][C:18]3=[O:34])[CH3:16])=[CH:11][CH:10]=2)=[CH:3]1.C1([SiH3])C=CC=CC=1.C([OH:45])(C)C.C(Cl)Cl>[Co]>[OH:45][C:31]([CH3:33])([CH3:32])[CH2:30][C@:20]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][CH2:22][CH2:23][N:17]([C@H:15]([C:12]2[CH:11]=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[CH:3]=3)=[CH:14][CH:13]=2)[CH3:16])[C:18](=[O:34])[NH:19]1

Komponenten

5

Edukt 3

HCID 12752PhenylsilaneHCID 21966342Isopropanol methylene chlorideHCID 59190381(S)-1-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-4-(2-methylallyl)-4-phenyl-1,3-diazepan-2-one

Produkt 1

HCID 59190389HCID 59190389, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 104730CobaltKatalysator

Versuchsvorschrift

To a solution of (S)-1-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-4-(2-methylallyl)-4-phenyl-1,3-diazepan-2-one (4 mg, 0.0088 mmol) in 2:1 i-Propanol/CH2Cl2 (2 mL) was added the cobalt catalyst A (c.a. 1 mg, cat. amount) and phenylsilane (100 μL, excess). The mixture was stirred vigorously in open air for 1 h. LC-MS found the reaction completed. The mixture was quenched by 1% aq HCl, concentrated and purified by prep HPLC to afford (S)-4-(2-hydroxy-2-methylpropyl)-1-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-4-phenyl-1,3-diazepan-2-one (1.4 mg, 34%). LC-MS Method 1 tR=1.56 min., m/z 473 (M+1); 1H NMR (CD3OD) δ 7.93 (s, 1H), 7.83 (dd, 1H), 7.56 (d, 2H), 7.40-7.34 (m, 4H), 7.27 (t, 1H), 7.16 (d, 2H), 6.62 (d, 1H), 5.46 (q, 1H), 3.63 (s, 3H), 2.93 (m, 1H), 2.76 (m, 1H), 2.39 (d, 1H), 1.52 (d, 3H), 1.17 (s, 3H), 0.59 (s, 3H).

Aufarbeitung

  1. customThe mixture was quenched by 1% aq HCl
  2. concentrationconcentrated
  3. custompurified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7fb26092dd3943daa8945f130cc2ae21
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202857B2

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