Sodium Carbonate → HCID 71086859, Verbindung

HRID 571828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571828
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[C:21]#[N:22].ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+].[NH2:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[C:45]#[N:46]>ClCCl.O>[C:17]([O:16][C:14]([N:10]1[CH2:11][CH2:12][O:13][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:27]([NH:41][C:42]3[CH:49]=[CH:48][CH:47]=[C:44]([C:45]#[N:46])[CH:43]=3)=[O:33])=[C:3]([C:21]#[N:22])[CH:4]=2)[CH2:9]1)=[O:15])([CH3:19])([CH3:18])[CH3:20]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 167023-AminobenzonitrileHCID 94429TriphosgeneHCID 86674686HCID 86674686, Verbindung

Produkt 1

HCID 71086859HCID 71086859, VerbindungAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of tert-butyl (RS)-2-(4-amino-3-cyanophenyl)morpholine-4-carboxylate (70 mg, example 28b) in dichloromethane (2 ml) was added triphosgene (25 mg). A solution of sodium carbonate (49 mg) in water (2 ml) was then added. The reaction mixture was stirred at room temperature for 3 hours. TLC showed all the starting material had reacted. 3-Aminobenzonitrile (28 mg, CAS 2237-30-1) was then added and the reaction mixture was stirred at room temperature for a further 40 hours. TLC showed the reaction was complete. The reaction mixture was poured into dichloromethane and extracted with water. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: 0% to 100% EtOAc in hexanes) to give (RS)-2-{3-cyano-4-[3-(3-cyano-phenyl)-ureido]-phenyl}-morpholine-4-carboxylic acid tert-butyl ester (16 mg, 16%) as a white solid. MS (ISP): 392.2 ([M+H—C4H8]+), 348.2 ([M+H—C4H8—CO2]+).

Aufarbeitung

  1. customhad reacted
  2. stirringthe reaction mixture was stirred at room temperature for a further 40 hours
  3. extractionextracted with water
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2; gradient: 0% to 100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-95ecaefb4cfd4daea11844f12515143e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029370B2

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