Hydrochloric Acid → HCID 42603128, compound

HRID 884071Notes

Reaction equation

HRID 884071 reaction equation
[CH3:1][N:2]([CH3:39])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:38])/[C:14](/[C:28]2[CH:33]=[CH:32][C:31]([O:34]COC)=[CH:30][CH:29]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][C:21]([O:24]COC)=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O.O>[CH3:39][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:38])/[C:14](/[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68731799HCID 68731799, compound

Product 1

HCID 42603128HCID 42603128, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4a (45 mg, 0.0842 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 2 h. A solution of NaHCO3 (126 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 residual solid was crystallized with Et2O to give 5 (68%). 5: colorless powder; 1H-NMR (CD3OD) δ 0.98 (3H, t, J=7.4 Hz), 2.45 (6H, s), 2.61 (2H, q, J=7.4 Hz), 2.90 (2H, t, J=5.3 Hz), 4.14 (2H, t, J=5.3 Hz), 6.54 (2H, d, J=8.8 Hz), 6.63 (2H, d, J=8.6 Hz), 6.92-6.97 (6H, m), 7.52 (2H, d, J=9.0 Hz). HRMS calcd for C27H31N2O4 [M+H]+: 447.2284. Found: 447.2298.

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 solid was crystallized with Et2O

Sources & evidence

ORD record
ord-46cb7555702e4a1a90bc8dd437a8185b
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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