Dichloromethane → 3-{4-[4-(2-amino-3-morpholin-4-yl-3-oxopropyl)-phenoxy]-phenyl}-N-hydroxypropionamide hydrochloride

HRID 748989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748989
C(OC(=O)[NH:7][CH:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33](=[O:36])[NH:34][OH:35])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])(C)(C)C.C(Cl)[Cl:39]>>[ClH:39].[NH2:7][CH:8]([C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([NH:34][OH:35])=[O:36])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1

Komponenten

3

Edukt 2

HCID 6344DichloromethaneHCID 59762804(1-{4-[4-(2-Hydroxycarbamoyl-ethyl)-phenoxy]-benzyl}-2-morpholin-4-yl-2-oxoethyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 159825743-{4-[4-(2-amino-3-morpholin-4-yl-3-oxopropyl)-phenoxy]-phenyl}-N-hydroxypropionamide hydrochlorideAusbeute 85 %

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

The compound 16 (1.1 g) was dissolved in CH2Cl2 (30 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 17 as a white amorphous solid (0.82 g, 85%). 1H NMR (400 MHz, DMSO-d6): 10.40 (s, 1H), 7.23 (overlapped d, J=8.8 Hz, 2H), 7.20 (overlapped d, J=8.8 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 6.89 (d, J=8.4 Hz, 2H), 4.62 (m, 1H), 3.35-3.54 (m, 8H), 2.91-3.07 (m, 2H), 2.80 (t, J=8.0 Hz, 2H), 2.25 (t, J=8.0 Hz, 2H); LCMS: Obsd.414, Calcd. 413.47.

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-235fc3b53c5244aead12ace6ad9edc38
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399786B2

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