Hydrochloric Acid → HCID 42603132, compound

HRID 884070Notes

Reaction equation

HRID 884070 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:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])\[CH2:16][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:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])\[CH2:16][CH3:17])=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68730465HCID 68730465, compound

Product 1

HCID 42603132HCID 42603132, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4a (75 mg, 0.153 mmol) in MeOH (2 ml) was added 4N HCl in 1,4-dioxane (0.4 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 residual was crystallized with AcOEt to give 5a (74%). 5a: colorless powder; 1H-NMR (CD3OD) δ 0.97 (3H, t, J=7.5 Hz), 2.09 (3H, s), 2.37 (6H, s), 2.58 (2H, q, J=7.5 Hz), 2.80 (2H, t, J=5.5 Hz), 4.11 (2H, t, J=5.5 Hz), 6.47 (2H, d, J=8.8 Hz), 6.90 (2H, d, J=9.1 Hz), 6.94 (2H, d, J=9.1 Hz), 7.05-7.15 (4H, m), 7.53 (2H, d, J=9.1 Hz). HRMS calcd for C28H33N2O3 [M+H]+: 445.2491. Found: 445.2497.

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 residual was crystallized with AcOEt

Sources & evidence

ORD record
ord-a2e3227c549c4a758d21d78c60d6cd5f
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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