Hydrochloric Acid → HCID 68731126, compound

HRID 884058Notes

Reaction equation

HRID 884058 reaction equation
[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:34])[CH:14]([C:24]2[CH:29]=[CH:28][C:27]([O:30]COC)=[CH:26][CH:25]=2)[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH3:17])=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O.O>[CH3:35][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:34])[CH:14]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH3:17])=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68732449HCID 68732449, compound

Product 1

HCID 68731126HCID 68731126, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3b (30 mg, 0.0632 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. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residue was crystallized with Et2O to give 8 (67%). 8: colorless powder; 1H-NMR (CD3OD) δ 1.53 (3H, dd, J=1.4, 6.8 Hz), 2.35 (6H, s), 2.77 (2H, t, J=5.4 Hz), 4.06 (2H, t, J=5.4 Hz), 4.64 (1H, brt), 5.53 (2H, dq, J=1.5, 6.8 Hz), 6.74 (2H, d, J=8.6 Hz), 6.85 (2H, d, J=9.2 Hz), 7.18-7.22 (5H, m), 7.27-7.32 (4H, m). HRMS calcd for C27H31N2O3 [M+H]+: 431.2335. Found: 431.2348.

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-2ad73de16711486ca7faa3cd6e147af6
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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