Dichloromethane → 3-{4-[4-(2-Amino-2-dimethylcarbamoylethyl)-phenoxy]-phenyl}-propionic acid hydrochloride

HRID 748982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748982
C(OC([NH:8][CH:9]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1)=O)(C)(C)C.C(Cl)[Cl:35]>>[ClH:35].[NH2:8][CH:9]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1

Komponenten

3

Edukt 2

HCID 6344DichloromethaneHCID 597628113-{4-[4-(2-Tert-butoxycarbonylamino-2-dimethylcarbamoyl-ethyl)-phenoxy]-phenyl}-propionic acid

Produkt 1

HCID 159824543-{4-[4-(2-Amino-2-dimethylcarbamoylethyl)-phenoxy]-phenyl}-propionic acid hydrochlorideAusbeute 87 %

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

The acid compound 6 (0.8 g) was dissolved in CH2Cl2 (20 mL) and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temperature for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×25 mL), decanted, and dried to yield the desired compound 10 as a white amorphous solid (0.6 g, 87%). 1H NMR (DMSO-d6): 12.20 (br, 1H), 7.24 (d, J=8.4 Hz, 2H), 7.21 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.8 Hz, 2H), 6.90 (d, J=8.0 Hz, 2H), 4.53 (m, 1H), 3.04 (dd, J=13.2 and 6.0 Hz, 1H), 2.95 (dd, J=14.0 and 8.0 Hz, 1H), 2.81 (m, 5H), 2.71 (s, 3H), 2.53 (t, J=7.6 Hz, 2H). LCMS (m/e): Obsd. 357.0, Calcd. 356.42

Aufarbeitung

  1. customHydrogen chloride gas was bubbled through this solution for 20 min
  2. customThe excess HCl was degassed
  3. customthe CH2Cl2 was removed
  4. customThe residual solid was triturated with EtOAc (2×25 mL)
  5. customdecanted
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-704b384940c84562afa8c148aac204b7
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399786B2

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