Dichloromethane → 2-amino-3-{4-[4-(2-hydroxycarbamoylethyl)-phenoxy]-phenyl}-N,N-dimethylpropionamide hydrochloride

HRID 748981Notes

Reaction equation

HRID 748981 reaction equation
C(OC(=O)[NH:7][CH:8]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](=[O:28])[NH:26][OH:27])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(Cl)[Cl:36]>>[ClH:36].[NH2:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25](=[O:28])[NH:26][OH:27])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)[C:29]([N:30]([CH3:31])[CH3:32])=[O:33]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 59762805(1-Dimethylcarbamoyl-2-{4-[4-(2-hydroxycarbamoyl-ethyl)-phenoxy]-phenyl}-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 159824522-amino-3-{4-[4-(2-hydroxycarbamoylethyl)-phenoxy]-phenyl}-N,N-dimethylpropionamide hydrochlorideYield 98%

Conditions

Temperature
2.5 °C

Procedure

The hydroxamate 8 (3.4 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 temperature 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 9 as a white amorphous solid (2.9 g, 98%). 1H NMR (DMSO-d6): 10.39 (s, 1H), 7.21 (d, J=8.4 Hz, 4H), 6.95 (d, J=8.4 Hz, 2H), 6.99 (d, J=8.4 Hz, 2H), 4.55 (m, 1H), 2.95-2.99 (m, 2H), 2.82 (s, 3H), 2.80 (t, J=8.0 Hz, 2H), 2.73 (s, 3H), 2.25 (t, J=8.0 Hz, 2H); LCMS (m/e): Obsd. 372.0, Calcd. 371.43

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-5b0a4c1d28924c8c9f65f0049730792f
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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