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Cesium carbonate → (S)-3-methyl-3-[4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 519154
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 519154
Br[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][C:10]1[N:5]2[CH:6]([CH3:25])[C:7](=[O:24])[N:8]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:9]=1.[C:26]([O:30][C:31]([N:33]1[CH2:37][CH2:36][C@@:35]([NH2:39])([CH3:38])[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:26]([O:30][C:31]([N:33]1[CH2:37][CH2:36][C@:35]([CH3:38])([NH:39][C:2]2[CH:3]=[C:4]3[C:13](=[CH:14][CH:15]=2)[O:12][CH2:11][C:10]2[N:5]3[CH:6]([CH3:25])[C:7](=[O:24])[N:8]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:9]=2)[CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86328910(S)-t-Butyl 3-amino-3-methylpyrrolidine-1-carboxylateHCID 867274626-Bromo-4-methyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

Produkt 1

HCID 86727547
(S)-3-methyl-3-[4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-pyrrolidine-1-carboxylic acid tert-butyl ester
Ausbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-4-methyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one ((Preparation #1, Step E, 2.184 g, 5.12 mmol) and (S)-3-amino-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.977 g, 4.88 mmol) in toluene (5 mL) was added Pd(OAc)2 (0.110 g, 0.488 mmol) and dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine (0.464 g, 0.976 mmol) followed by cesium carbonate (3.18 g, 9.76 mmol) and the reaction mixture was heated at reflux overnight. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 50% EtOAc in petroleum ether) to give (S)-3-methyl-3-[4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]pyrrolidine-1-carboxylic acid tert-butyl ester (1 g, 38%). 1H NMR (400 MHz, CDCl3) δ 6.85 (m, 1H), 6.34-6.28 (m, 2H), 5.11 (m, 2H), 4.70-4.52 (m, 3H), 3.68 (m, 2H), 3.70-3.35 (m, 4H), 2.20 (m, 1H), 1.88 (m, 1H), 1.46 (m., 12H), 1.05 (m, 2H), 0.03 (s, 9H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (eluting with 50% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-b901afe7525f496c80665d2a13644b41
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115151B2

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