Hydrochloric Acid → 4-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-5,6-dihydro-2H-pyridine-1,3-dicarboxylic Acid 1-tert-butyl Ester

HRID 2428197Notes

Reaction equation

HRID 2428197 reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[CH2:8][N:9]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:10][CH2:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][C:23]2[C:28]([Cl:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=2[Cl:31])=[CH:15][CH:14]=1)=[O:6].Cl>C1COCC1>[C:35]([O:34][C:32]([N:9]1[CH2:10][CH2:11][C:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][C:23]3[C:28]([Cl:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=3[Cl:31])=[CH:15][CH:14]=2)=[C:7]([C:5]([OH:6])=[O:4])[CH2:8]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 671486554-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-5,6-dihydro-2H-pyridine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl Ester

Product 1

HCID 671489034-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-5,6-dihydro-2H-pyridine-1,3-dicarboxylic Acid 1-tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Aq. 1M LiOH (11.1 mL, 11.1 mmol) was added to a sol. of compound C3 (1.50 g, 2.72 mmol) in THF (10 mL). The mixture was stirred at 60° C. for 3 days. The mixture was allowed to cool to rt, and aq. 1M HCl was added, until the mixture was acidic. The mixture was extracted with EtOAc. The org. extracts were washed with aq. 1M HCl and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (heptane/EtOAc 1:2) yielded the title compound mixed with 4-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-3,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester (1.41 g, 99%). LC-MS: tR=1.10 min; ES+: 522.30.

Workup

  1. temperatureto cool to rt
  2. extractionThe mixture was extracted with EtOAc
  3. washextracts were washed with aq. 1M HCl and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the crude by FC (heptane/EtOAc 1:2)

Sources & evidence

ORD record
ord-9eabb35990cf4781b3205f6a4ee5a254
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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