Hydrochloric Acid → HCID 71062250, compound

HRID 529034Notes

Reaction equation

HRID 529034 reaction equation
[CH2:1]([N:5]([CH2:36][CH2:37][CH2:38][CH3:39])[C:6]([C:8]1[N:13]=[C:12]([C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][C:15]=2[C:24]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27]2)=[O:25])[CH:11]=[CH:10][CH:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>C1COCC1.CO>[CH2:1]([N:5]([CH2:36][CH2:37][CH2:38][CH3:39])[C:6]([C:8]1[N:13]=[C:12]([C:14]2[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=2[C:24]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27]2)=[O:25])[CH:11]=[CH:10][CH:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71060819HCID 71060819, compound

Product 1

HCID 71062250HCID 71062250, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(6-(dibutylcarbamoyl)pyridin-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (158 mg, 0.30 mmol) in THF (2.0 mL) and MeOH (2.0 mL) was added 2N NaOH (1.5 mL, 3.00 mmol). The resulting reaction mixture was stirred at room temperature for 2 h. At 0° C., the reaction mixture was neutralized to pH 4-5 with 1N HCl. The solution was extracted with EtOAc (3×) and the combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound (146 mg, 95%). MS(ESI+) m/z 514.4 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customAt 0° C.
  3. extractionThe solution was extracted with EtOAc (3×)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5bba6ad0c65c43fa8d7214864371cf98
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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