Sodium Hydroxide → HCID 18765938, compound

HRID 481006Notes

Reaction equation

HRID 481006 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][C:20]([O:22]C)=[O:21])[NH:12][C:11]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[C:10]1[C:38]([O:40][CH3:41])=[O:39].[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:10]([C:38]([O:40][CH3:41])=[O:39])=[C:11]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][CH2:33][CH2:34][N:35]([CH3:36])[CH3:37])[NH:12][C:13]([CH2:19][C:20]([OH:22])=[O:21])=[C:14]1[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18765853HCID 18765853, compound

Product 1

HCID 18765938HCID 18765938, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of dimethyl 4-(2,6-dichlorophenyl)-2-(2-{2-[3-(dimethylamino)propyl]phenyl}ethyl)-6-(2-methoxy-2-oxoethyl)-1,4-dihydro-3,5-pyridinedicarboxylate (4.31 g, 7.14 mmol) in 1,4-dioxane (61 ml) was added 2N NaOH. The reaction mixture was stirred at room temperature for 2.5 h. The residual 1,4-dioxane was removed by evaporation in vacuo. The residue was diluted with water (19 ml) and washed with diethyl ether (50 ml×2) and AcOEt (20 ml). The water phase was then acidified with aq. NaH2PO4 to about pH 5. The whole was extracted with CH2Cl2 (300 ml×3). The combined extract was washed with brine, dried over MgSO4, and concentrated to afford the desired acid (4.30 g, 90% yield) as a yellow amorphous.

Workup

  1. customThe residual 1,4-dioxane was removed by evaporation in vacuo
  2. additionThe residue was diluted with water (19 ml)
  3. washwashed with diethyl ether (50 ml×2) and AcOEt (20 ml)
  4. extractionThe whole was extracted with CH2Cl2 (300 ml×3)
  5. extractionThe combined extract
  6. washwas washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e36f7ac411f34ebf92489ff7199d48ff
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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