Hydrochloric Acid → HCID 60206862, compound

HRID 1296116Notes

Reaction equation

HRID 1296116 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, 1H), 7.37 (m, 2H), 7.28 (m, 1H), 6.59 (s, 1H), 6.40 (m, 1H), 6.31 (m, 1H), 4.0 (m, 1H), 3.79 (m, 1H), 2.95 (m, 2H), 2.63 (m, 4H), 2.44 (m, 1H), 2.05 (m, 2H), 1.90 (s, 3H), 1.79 (m, 2H), 1.59 (m, 1H), 1.5–1.3 (m, 3H), 1.26 (d, J=7 Hz, 6H); 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-bee935488a5a4ef086d72f9d8654e4ae
Source dataset
uspto-grants-2007_07
Patent number
US07244725B2

Reaction notes

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