1,2-Dichloroethane → HCID 45279987, Verbindung

HRID 1799799

Reaktionsgleichung

Reaktionsgleichung von HRID 1799799
[CH2:1]([Cl:4])[CH2:2]Cl.NC1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([CH3:15])([OH:14])[CH3:13])=[C:8]([O:18][CH3:19])[CH:7]=1.[C:20]([O-:23])([O-])=O.[K+].[K+].[CH3:26][N:27]([CH:29]=[O:30])[CH3:28]>CCOC(C)=O>[Cl:4][C:1]1[CH:2]=[CH:16][C:9]([C:20]2[O:23][C:13]3[C:29](=[O:30])[N:27]([C:28]4[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([OH:14])([CH3:13])[CH3:15])=[C:8]([O:18][CH3:19])[CH:7]=4)[CH2:26][C:12]=3[CH:11]=2)=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 595950521-(4-Amino-2-methoxyphenoxy)-2-methylpropan-2-ol

Produkt 1

HCID 45279987HCID 45279987, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of Part D product (40 mg, 0.127 mmol), EDC (48.6 mg, 0.254 mmol) and 1-(4-amino-2-methoxyphenoxy)-2-methylpropan-2-ol (26.8 mg, 0.127 mmol) in DMF (1.0 mL) was stirred at RT overnight. After K2CO3(35.0 mg, 0.254 mmol) was added, the reaction was stirred overnight. Then the mixture was diluted with EtOAc (˜25 mL), washed with water and brine, dried over anhydrous Na2SO4, and concentrated. The resulting brown solution was purified by prep. HPLC to give 10 mg of the title compound as a white solid after lyophilization: 1H NMR (400 MHz, CDCl3) δ7.72 (d, J=8.3 Hz, 2H), 7.60 (s, 1H), 7.42 (d, J=8.3 Hz, 2H), 6.94 (br. s., 2H), 6.80 (s, 1H), 4.66 (s, 2H), 3.91 (s, 3H), 3.83 (s, 2H), 1.34 (s, 6H); HPLC retention time: 2.918 min; LCMS (ES): m/z 428 [M+H]+.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe resulting brown solution was purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-8c131d8026e940cb98d119789ddb4b0f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344160B2

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