Dichloromethane → HCID 15982712, compound

HRID 749019Notes

Reaction equation

HRID 749019 reaction equation
C(OC([NH:8][CH:9]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=O)(C)(C)C.C(Cl)[Cl:34]>>[ClH:34].[NH2:8][CH:9]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 69113715HCID 69113715, compound

Product 1

HCID 15982712HCID 15982712, compoundYield 83%

Conditions

Temperature
2.5 °C

Procedure

The acid compound 46 (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 (2×25 mL), decanted, and dried to yield the desired compound 50 as a white amorphous solid (0.64 g, 83%). 1H NMR (DMSO-d6): 12.2 (br, 1H), 7.62 (d, J=8.4 Hz, 2H), 7.56 (d, J=8.0 Hz, 2H), 7.31 (d, J=8.4 Hz, 2H), 7.29 (d, J=8.0 Hz, 2H), 4.58 (m, 1H), 3.02-3.08 (m, 2H), 2.85 (t, J=7.6 Hz, 2H), 2.81 (s, 3H), 2.71 (s, 3H), 2.57 (t, J=7.6 Hz, 2H).LCMS (m/e): Obsd. [MH]+ 341, Calcd. 340.4.

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

Sources & evidence

ORD record
ord-ef915293697c4b2f841fe820aa89dfed
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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