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

HRID 2428199Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of compound C6 (1.00 g, 1.86 mmol) and aq. 1M LiOH (7.00 mL, 7.00 mmol) in THF (7.00 mL) was stirred at 70° C. overnight. Aq. 1M HCl was added until a pH of 4 was reached, and the mixture was extracted with EtOAc (3×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying under high vacuum yielded the crude title compound mixed with 6-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-3′,6′-dihydro-2′H-[3,4′]bipyridinyl-1′,3′-dicarboxylic acid 1′-tert-butyl ester (850 mg, 87%) that was used further without purification.

Workup

extractionthe mixture was extracted with EtOAc (3×)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customDrying under high vacuum

Sources & evidence

ORD record: ord-740d9fe7c4324483b614a0276a860688
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968720B2

Reaction notes

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