Methanol → 1-Methyl-3-{N-[[beta-[3,4-bis(isobutyryloxy)phenyl]ethyl]]carbamoyl}-1,4-dihydropyridine

HRID 260206

Reaction equation

HRID 260206 reaction equation
FC(F)(F)C([O-])=O.[CH3:8][N+:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:37])[NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[C:21]([O:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:20]=2)[CH:10]=1.CO.C([O-])(O)=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.CCOCC>[CH3:8][N:9]1[CH:14]=[CH:13][CH2:12][C:11]([C:15](=[O:37])[NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[C:21]([O:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:20]=2)=[CH:10]1

Participants

7

Reactant 4

HCID 887MethanolHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 140504311-methyl-3-{N-[[beta-[3,4-bis(isobutyryloxy)phenyl]ethyl]]carbamoyl}-pyridinium trifluoroacetate

Product 1

HCID 140504301-Methyl-3-{N-[[beta-[3,4-bis(isobutyryloxy)phenyl]ethyl]]carbamoyl}-1,4-dihydropyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.55 g (1 mmol) of 1-methyl-3-{N-[[β-[3,4-bis(isobutyryloxy)phenyl]ethyl]]carbamoyl}pyridinium trifluoroacetate in 50 ml of deaerated water containing 10 ml of methanol was extracted three times with 30 ml portions of ether. To the resultant aqueous solution was added NaHCO3 (0.25 g, 3 mmol) and 50 ml of ethyl ether and the mixture was kept under nitrogen. To this ice-cold mixture was added sodium dithionite (0.52 g, 3 mmol) and the mixture was stirred vigorously for 30 minutes. The ether layer was separated and the aqueous layer was extracted twice with ether. The combined ether extracts were washed with water and dried over sodium sulfate. Ether was removed under vacuum, leaving an oily product. NMR analysis confirmed that the product has the structural formula: ##STR1493##

Workup

  1. customThe ether layer was separated
  2. extractionthe aqueous layer was extracted twice with ether
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. customEther was removed under vacuum
  6. customleaving an oily product

Sources & evidence

ORD record
ord-1418fbb523584afb98e426d862b16a6d
Source dataset
uspto-grants-1996_06
Patent number
US05525727

Linked notes

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