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

HRID 749007ノート

反応式

HRID 749007 の反応式
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

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
2.5 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-714ba387ddbf499db14cdfc605c093d3
出典データセット
uspto-grants-2008_07
特許番号
US07399786B2

反応ノート

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