Methyl chloroformate → 3-Acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid-methyl ester

HRID 133541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133541
[CH3:1][C:2]1[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[C:11]3[CH2:10][CH2:9][NH:8][CH2:7][C:6]=3[S:5][C:4]=2[N:3]=1.Cl[C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:28][O:27][C:25]([N:8]1[CH2:7][C:6]2[S:5][C:4]3[N:3]=[C:2]([CH3:1])[C:14]([C:15](=[O:17])[CH3:16])=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]=3[C:11]=2[CH2:10][CH2:9]1)=[O:26]

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 688965541-(2-Methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone

Produkt 1

HCID 115670903-Acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid-methyl esterAusbeute 394,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 50 mg (0.15 mmol) 1-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone (the preparation of which is described in example 23) in 5 ml dichloromethane was added 0.02 ml (0.022 mmol) methyl chloroformate and 32 mg (0.022 mmol) potassium carbonate. The mixture was stirred at RT for 1 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 1:1) afforded 33 mg (56%) 3-Acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid-methyl ester as a light yellow solid. ES-MS m/e (%): 381 (M+H+, 100);

Aufarbeitung

  1. additionpoured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c7927c90bcfa4bd096c0d9c99206df9d
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390903B2

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