Dichloromethane → HCID 16004795, compound

HRID 273429Notes

Reaction equation

HRID 273429 reaction equation
[CH2:1]([O:8][C:9](=[O:37])[CH:10]([NH:29]C(OC(C)(C)C)=O)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:28])[NH:26][OH:27])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)[Cl:39]>>[ClH:39].[CH2:1]([O:8][C:9](=[O:37])[CH:10]([NH2:29])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:28])[NH:26][OH:27])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 72575119HCID 72575119, compound

Product 1

HCID 16004795HCID 16004795, compoundYield 71.4%

Conditions

Temperature
2.5 °C

Procedure

The hydroxamate 5 (0.4 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 6 as a white amorphous solid (0.25 g, 71.4%). 1H NMR (DMSO-d6): 11.18 (s, 1H), 7.78 (d, J=8.8 Hz, 2H), 7.31-7.39 (m, 5H), 7.24 (d, J=8.4 Hz, 2H), 6.99 (d, J=8.4 Hz, 2H), 6.98 (d, J=8.8 Hz, 2H), 5.19 (s, 2H), 4.40 (m, 1H), 3.07-3.18 (m, 2H) LCMS (m/e): Obsd, 407.0; Calcd, 406.43.

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-373d26b6110a4468a8dfec9497b7db33
Source dataset
uspto-grants-2008_11
Patent number
US07456292B2

Reaction notes

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