Hydrochloric Acid → HCID 25265838, compound

HRID 884057Notes

Reaction equation

HRID 884057 reaction equation
[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:35])/[C:15](/[C:25]2[CH:30]=[CH:29][C:28]([O:31]COC)=[CH:27][CH:26]=2)=[C:16](/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)\[CH2:17][CH3:18])=[CH:9][CH:8]=1.Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O.O>[CH3:36][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:35])/[C:15](/[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:16](/[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)\[CH2:17][CH3:18])=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68731330HCID 68731330, compound

Product 1

HCID 25265838HCID 25265838, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6b (55 mg, 0.113 mmol) in MeOH (0.5 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 7b (76%). 7b: colorless powder; 1H-NMR (CD3OD) δ 0.97 (3H, t, J=7.4 Hz), 1.99 (2H, m), 2.35 (6H, s), 2.59-2.66 (4H, m), 4.02 (2H, t, J=6.1 Hz), 6.51 (2H, d, J=8.8 Hz), 6.90 (2H, d, J=9.2 Hz), 6.92 (2H, d, J=8.8 Hz), 7.12-7.23 (5H, m), 7.50 (2H, d, J=9.2 Hz). HRMS calcd for C28H33N2O3 [M+H]+: 445.2491. Found: 445.2507.

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-0a5dbfd56760422ca29726e0a21faa88
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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