Water → 1-Methyl-3-{N-[beta-(3,4-dipivalyloxyphenyl)ethyl]}carbamoyl-1,4-dihydropyridine

HRID 1199554Notes

Reaction equation

HRID 1199554 reaction equation
[I-].[CH3:2][N+:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9](=[O:33])[NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[C:15]([O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH:14]=2)[CH:4]=1.O.C(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CO.C(OCC)(=O)C>[CH3:2][N:3]1[CH:8]=[CH:7][CH2:6][C:5]([C:9](=[O:33])[NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[C:15]([O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH:14]=2)=[CH:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 13473425HCID 13473425, compound

Product 1

HCID 100720521-Methyl-3-{N-[beta-(3,4-dipivalyloxyphenyl)ethyl]}carbamoyl-1,4-dihydropyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold mixture of 2.0 g (3.5 mmol) of compound 6c, 200 ml of deaerated water and 100 ml of ethyl acetate, 1.14 g (14 mmol) of sodium bicarbonate and 2.43 g (14 mmol) of sodium dithionite were added. The mixture was stirred under N2 for 20 mins. The ethyl acetate layer was separated and the aqueous layer was re-extracted with 100 ml of ethyl acetate. The combined ethyl acetate was washed with cold deaerated water, dried over anhydrous Na2SO4 and distilled on rotovapor. The viscous yellow oily residue was dissolved in 5 ml of acetone, filtered under N2 atmosphere and then evaporated under reduced pressure. The solid residue was dried under vacuum over P2O5 in N2 atmosphere. It reduced alcoholic AgNO3 instantaneously and gave no color with DeCl3 test. Yield, 1.3 g (83%) m.p. 45°-48° C.; UV (CH3OH) 210 and 355 nm; NMR (CDCl3) δ 7.04-6.92 (m, 4H, C6H3 +C2 dihydropyridine proton), 5.71-5.61 (doublet of doublets, 1H, C6 dihydropyridine proton), 4.81 (bs, 1H, CONH), 4.60-4.51 (m, 1H, C5 dihydropyridine proton), 3.53 (q, 2H, J=6.3 Hz, --N--CH2), 2.36 (bs, 2H, C4 dihydropyridine proton), 2.91 (s, 3H, N--CH3), 2.79 (t, 2H, J=6.3 Hz, CH2), 1.33 (s, 18H, CO--C(CH3)3). Anal. Calcd for C25H34N2O5. 11/2H2O: C, 63.9; H, 7.93; N, 5.96. Found: C, 63.4; H, 7.81; N, 5.94.

Workup

  1. additionwere added
  2. customThe ethyl acetate layer was separated
  3. extractionthe aqueous layer was re-extracted with 100 ml of ethyl acetate
  4. washThe combined ethyl acetate was washed with cold deaerated water
  5. dry with materialdried over anhydrous Na2SO4
  6. distillationdistilled on rotovapor
  7. dissolutionThe viscous yellow oily residue was dissolved in 5 ml of acetone
  8. filtrationfiltered under N2 atmosphere
  9. customevaporated under reduced pressure
  10. dry with materialThe solid residue was dried under vacuum over P2O5 in N2 atmosphere
  11. customgave no color with DeCl3 test
  12. customYield

Sources & evidence

ORD record
ord-15545bd53ebe4bddb2a15fb38d25e88a
Source dataset
uspto-grants-1990_02
Patent number
US04900837

Reaction notes

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