Hydrochloric Acid → HCID 42603177, compound

HRID 884062Notes

Reaction equation

HRID 884062 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)\[CH2:16][CH2:17][CH3:18])=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O.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)\[CH2:16][CH2:17][CH3:18])=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68731540HCID 68731540, compound

Product 1

HCID 42603177HCID 42603177, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5a (45 mg, 0.0921 mmol) in MeOH (1 ml) was added 3N HCl in AcOEt (0.5 ml) under ice cooling, and the mixture was stirred at room temperature for 1 h. A solution of NaHCO3 (139 mg) in H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt and a little MeOH. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residue was crystallized with Et2O to give 6a (83%). 6a: colorless powder; 1H-NMR (CD3OD) δ 0.87 (3H, t, J=7.4 Hz), 1.38 (2H, m), 2.46 (6H, s), 2.59 (2H, m), 2.91 (2H, t, J=5.1 Hz), 4.14 (2H, t, J=5.1 Hz), 6.51 (2H, d, J=8.6 Hz), 6.92-6.96 (4H, m), 7.10-7.24 (5H, m), 7.53 (2H, d, J=8.8 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-714c3b99837341d8829508a07040f7c0
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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