Dichloromethane → HCID 15982710, compound

HRID 749018Notes

Reaction equation

HRID 749018 reaction equation
C(OC(=O)[NH:7][CH:8]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([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:12][CH:11]=1)(C)(C)C.C(Cl)[Cl:35]>>[ClH:35].[NH2:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24](=[O:27])[NH:25][OH:26])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[C:28]([N:29]([CH3:31])[CH3:30])=[O:32]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 72551664HCID 72551664, compound

Product 1

HCID 15982710HCID 15982710, compoundYield 88%

Conditions

Temperature
2.5 °C

Procedure

The hydroxamate 48 (0.9 g) was dissolved in CH2Cl2 (25 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 (2×30 mL), decanted, and dried to yield the desired compound 49 as a white amorphous solid (0.68 g, 88%). 1H NMR (DMSO-d6): 10.45 (s, 1H), 7.61 (d, J=8.4 Hz, 2H), 7.57 (d, J=8.0 Hz, 2H), 7.29 (d, J=8.4 Hz, 2H), 4.58 (m, 1H), 3.09 (dd, J=14.0 and 8.4 Hz, 1H), 3.01 (dd, J=14.0 and 7.2 Hz, 1H), 2.84 (t, J=6.8 Hz, 2H), 2.81 (s, 3H), 2.71 (s, 3H), 2.29 (t, J=7.2 Hz, 2H). LCMS (m/e): Obsd. [MH]+ 356, Calcd. 355.4

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 (2×30 mL)
  5. customdecanted
  6. customdried

Sources & evidence

ORD record
ord-07313412cc674bc78aba7430a282e768
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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