Hydrochloric Acid → HCID 60206862, compound

HRID 1985073Notes

Reaction equation

HRID 1985073 reaction equation
[ClH:1].C([O:9][C:10]1[CH:11]=[C:12]([CH:38]=[C:39]([F:41])[CH:40]=1)[CH2:13][C@H:14]([NH:34][C:35](=[O:37])[CH3:36])[C@H:15]([OH:33])[CH2:16][NH:17][C:18]1([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)C1C=CC=CC=1.[H][H].Cl>C(O)C.[Pd]>[ClH:1].[OH:9][C:10]1[CH:11]=[C:12]([CH:38]=[C:39]([F:41])[CH:40]=1)[CH2:13][C@H:14]([NH:34][C:35](=[O:37])[CH3:36])[C@H:15]([OH:33])[CH2:16][NH:17][C:18]1([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68538847HCID 68538847, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 60206862HCID 60206862, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 10 (0.70 g, 1.2 mmol) in 70 mL of ethanol in a Parr bottle is added 0.33 g of 10% palladium on carbon. The mixture is placed under 20 psi of hydrogen and shaken for 21 h. The mixture is filtered and the catalyst is washed with ethanol. Concentration in vacuo affords a colorless oil, which is treated with ethereal HCl to give a quantitiative yield of hydrochloride 11 as a white solid: 1H NMR (CDCl3+CD3OD drop) δ 7.44 (s, 1 H), 7.37 (m, 2 H), 7.28 (m, 1 H), 6.59 (s, 1 H), 6.40 (m, 1 H), 6.31 (m, 1 H), 4.0 (m, 1 H), 3.79 (m, 1 H), 2.95 (m, 2 H), 2.63 (m, 4 H), 2.44 (m, 1 H), 2.05 (m, 2 H), 1.90 (s, 3 H), 1.79 (m, 2 H), 1.59 (m, 1 H), 1.5-1.3 (m, 3 H), 1.26 (d, J=7 Hz, 6 H); MS (CI) m/z 457.4 (MH+).

Workup

  1. filtrationThe mixture is filtered
  2. washthe catalyst is washed with ethanol
  3. concentrationConcentration in vacuo
  4. customaffords a colorless oil, which

Sources & evidence

ORD record
ord-9a17b8868b664afb9bfa2290af9f31f7
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

Loading…