Dichloromethane → HCID 16004792, compound

HRID 273436Notes

Reaction equation

HRID 273436 reaction equation
C(OC(=O)[NH:7][CH:8]([C:27](=[O:31])[N:28]([CH3:30])[CH3:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:26])[NH:24][OH:25])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(Cl)[Cl:34]>>[ClH:34].[NH2:7][CH:8]([C:27](=[O:31])[N:28]([CH3:30])[CH3:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([NH:24][OH:25])=[O:26])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 72575117HCID 72575117, compound

Product 1

HCID 16004792HCID 16004792, compound

Conditions

Temperature
2.5 °C

Procedure

The hydroxamate 12 (0.8 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 (2×25 mL), decanted, and dried to yield the desired compound 13 as a white amorphous solid (0.34 g,). 1H NMR (DMSO-d6): 11.20 (s, 1H), 7.76 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.8 Hz, 2H), 7.02 (d, J=8.4 Hz, 2H), 6.95 (d, J=8.8 Hz, 2H), 4.52 (m, 1H), 2.92-3.05 (m, 1H), 2.76 (s, 3H), 2.71 (s, 3H). LCMS: Obsd 344.0, calcd 343.48.

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 (2×25 mL)
  5. customdecanted
  6. customdried

Sources & evidence

ORD record
ord-e23b247d44fe4937bcd3d2a8401adf53
Source dataset
uspto-grants-2008_11
Patent number
US07456292B2

Reaction notes

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