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

HRID 749007Notes

Reaction equation

HRID 749007 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
2.5 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-714ba387ddbf499db14cdfc605c093d3
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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