Dichloromethane → 3-{4-[4-(aminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-N-hydroxypropionamide hydrochloric acid salt

HRID 749007노트

반응식

HRID 749007 반응식
C(OC(=O)[NH:7][CH:8]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](=[O:27])[NH:25][OH:26])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)(C)(C)C.C(Cl)[Cl:35]>>[ClH:35].[NH2:7][CH:8]([C:28](=[O:32])[N:29]([CH3:30])[CH3:31])[C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]([NH:25][OH:26])=[O:27])=[CH:20][CH:21]=2)=[CH:13][CH:14]=1

참가 물질

3

반응물 2

HCID 6344DichloromethaneHCID 59751091(Dimethylcarbamoyl-{4-[4-(2-hydroxycarbamoyl-ethyl)-phenoxy]-phenyl}-methyl)-carbamic acid tert-butyl ester

생성물 1

HCID 159825803-{4-[4-(aminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-N-hydroxypropionamide hydrochloric acid salt수율 92%

반응 조건

온도
2.5 °C

실험 절차

The hydroxamate 35 (1.1 g) was dissolved in CH2Cl2 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 temp for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×50 mL), decanted, and dried to yield the desired compound 36 as a white amorphous solid (0.87 g, 92%). 1H NMR (DMSO-d6): 10.44 (s, 1H), 7.46 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.8 Hz, 2H), 7.03 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.4 Hz, 2H), 5.48 (d, J=5.2 Hz, 1H), 2.89 (s, 3H), 2.82 (s, 3H), 2.81 (t, J=8.0 Hz, 2H), 2.26 (t, J=8.0 Hz, 2H). LCMS (m/e): Obsd. [M+Na]+ 380, Calcd. 357.4

후처리

  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 (2×50 mL)
  5. customdecanted
  6. customdried

출처 및 근거

ORD 기록
ord-714ba387ddbf499db14cdfc605c093d3
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399786B2

반응 노트

불러오는 중…