Hydrochloric Acid → HCID 42603178, compound

HRID 884063Notes

Reaction equation

HRID 884063 reaction equation
[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:35])/[C:14](/[C:25]2[CH:30]=[CH:29][C:28]([O:31]COC)=[CH:27][CH:26]=2)=[C:15](/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)\[CH:16]([CH3:18])[CH3:17])=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO.O1CCOCC1.O>[CH3:36][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:35])/[C:14](/[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:15](/[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)\[CH:16]([CH3:18])[CH3:17])=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68729304HCID 68729304, compound

Product 1

HCID 42603178HCID 42603178, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5b (90 mg, 0.184 mmol) in MeOH (3 ml) was added 4N HCl in 1,4-dioxane (0.5 ml) under ice cooling, and the mixture was stirred at room temperature for 2 h. A solution of NaHCO3 in H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residue was crystallized with Et2O to give 6b (84%). 6b: colorless powder; 1H-NMR (CD3OD) δ 1.07 (6H, d, J=6.8 Hz), 2.37 (6H, s), 2.79 (2H, t, J=5.4 Hz), 3.12 (1H, sep, J=5.4 Hz), 4.11 (2H, t, J=5.4 Hz), 6.46 (2H, d, J=8.8 Hz), 6.94 (2H, d, J=9.1 Hz), 6.95 (2H, d, J=8.8 Hz), 7.10 (2H, m), 7.16-7.25 (3H, m), 7.52 (2H, d, J=9.1 Hz). HRMS calcd for C28H33N2O3 [M+H]+: 445.2491. Found: 445.2510.

Workup

  1. extractionthe whole was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was crystallized with Et2O

Sources & evidence

ORD record
ord-4385bdfc25c94d54bbfd34cc2833791a
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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