Hydrochloric Acid → HCID 68732761, compound

HRID 884074Notes

Reaction equation

HRID 884074 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])/[C:14](/[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30]COC)[CH:25]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO.O1CCOCC1.O>[CH3:35][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:34])/[C:14](/[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)=[C:15](/[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)\[CH2:16][CH3:17])=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68732973HCID 68732973, compound

Product 1

HCID 68732761HCID 68732761, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4a (50 mg, 0.105 mmol) in MeOH (2 ml) was added 4N HCl in 1,4-dioxane (0.26 ml) under ice cooling, and the mixture was stirred at room temperature for 3 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 (73%). 5a: colorless powder; 1H-NMR (CD3OD) δ 0.97 (3H, t, J=7.5 Hz), 2.36 (6H, s), 2.66 (2H, q, J=7.5 Hz), 2.79 (2H, t, J=5.4 Hz), 4.10 (2H, t, J=5.4 Hz), 6.52 (1H, dd, J=1.0, 8.1 Hz), 6.57 (1H, m), 6.64 (1H, m), 6.90 (1H, t, J=7.8 Hz), 6.94 (2H, d, J=9.1 Hz), 7.13-7.23 (5H, m), 7.53 (2H, d, J=9.1 Hz). HRMS calcd for C27H31N2O3 [M+H]+: 431.2335. Found: 431.2336.

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-a3a1a8fa6e0d48c792324c9e873977c7
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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