Tetrahydrofuran → HCID 86731028, Verbindung

HRID 2280212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280212
[C:1]([C:3]1[C:7]2[CH2:8][C@@H:9]3[C@@H:14]([CH2:15][C:6]=2[S:5][C:4]=1[N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[N:13]([CH3:16])[CH2:12][C@H:11]([C:17](=[O:22])[NH:18][CH2:19][CH2:20][CH3:21])[CH2:10]3)#[N:2].O1CCCC1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.Cl[C:53]([O:55][C:56]1[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=1)=[O:54]>C(OCC)(=O)C.O>[C:26]([O:25][C:24]([N:23]([CH3:31])[C:4]1[S:5][C:6]2[CH2:15][C@@H:14]3[C@H:9]([CH2:10][C@@H:11]([C:17]([N:18]([CH2:19][CH2:20][CH3:21])[C:53](=[O:54])[O:55][C:56]4[CH:57]=[CH:58][C:59]([N+:62]([O-:64])=[O:63])=[CH:60][CH:61]=4)=[O:22])[CH2:12][N:13]3[CH3:16])[CH2:8][C:7]=2[C:3]=1[C:1]#[N:2])=[O:30])([CH3:29])([CH3:28])[CH3:27]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 821294-Nitrophenyl chloroformateHCID 23700795NaHMDS tetrahydrofuranHCID 86731026HCID 86731026, Verbindung

Produkt 1

HCID 86731028HCID 86731028, VerbindungAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-8-methyl-6-(propylcarbamoyl)-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-2-yl]-N-methylcarbamate (412 mg) and tetrahydrofuran (5 mL) was added a 1 mol/L sodium hexamethyldisilazide-tetrahydrofuran solution (1.2 mL) at −40° C. After stirring at the same temperature for 20 minutes, 4-nitrophenyl chloroformate (242 mg) was added to the mixture, and then stirred for 1 hour. After warming to room temperature and stirring for 1.5 hours, water and ethyl acetate were added. After the separated organic layer was dried over anhydrous sodium sulfate, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 80%-100% ethyl acetate/hexane, gradient elution) to give 4-nitrophenyl N-{[(4aR*,6R*,8aR*)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-N-propylcarbamate (405 mg).

Aufarbeitung

  1. stirringstirred for 1 hour
  2. stirringstirring for 1.5 hours
  3. dry with materialAfter the separated organic layer was dried over anhydrous sodium sulfate, it
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: 80%-100% ethyl acetate/hexane, gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-433f9602b3144fd3b9b26f4e8bbf0a24
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09138434B2

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