Dichloromethane → HCID 15982576, compound

HRID 748994Notes

Reaction equation

HRID 748994 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36](=[O:39])[NH:37][OH:38])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:19])[CH3:18])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.C(Cl)[Cl:42]>>[ClH:42].[C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:9](=[O:10])[CH:8]([NH2:7])[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([NH:37][OH:38])=[O:39])=[CH:30][CH:29]=3)=[CH:25][CH:26]=2)[CH2:12][CH2:13]1)(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 59762809HCID 59762809, compound

Product 1

HCID 15982576HCID 15982576, compoundYield 85%

Conditions

Temperature
2.5 °C

Procedure

The acid compound 21 (0.8 g) was dissolved in CH2Cl2 (30 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 22 as a white amorphous solid (0.82 g, 85%). 1H NMR (CD3OD): 7.26 (overlapped d, J=8.8 Hz, 1H), 7.25 (overlapped d, J=8.8 Hz, 1H), 7.20 (d, J=8.8 Hz, 2H), 6.97 (overlapped d, J=8.4 Hz, 1H), 6.95 (overlapped d, J=8.4 Hz, 1H), 6.89 (overlapped d, J=8.4 Hz, 1H), 6.88 (overlapped d, J=8.4 Hz, 1H), 4.65 (m, 1H), 3.3-3.6 (m, 6H), 3.0-2.8 (m, 4H), 2.91 (t, J=7.6 Hz, 2H), 2.39 (t, J=7.6 Hz, 2H), 2.10(d, J=11.2 Hz, 3H). LCMS: Obsd. 455.0, Calcd. 454.52

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-e619ba19a28541abbc6a7d1069d71207
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

Loading…