Sodium Hydroxide → HCID 19093675, compound

HRID 1587510Notes

Reaction equation

HRID 1587510 reaction equation
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:53]([O:55]CC)=[O:54])[C:7](=[O:52])[N:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[N:29]=[N:30][N:31]([C:33]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:32]=2)=[CH:18][CH:17]=1)[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:53]([OH:55])=[O:54])[C:7](=[O:52])[N:8]2[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[N:29]=[N:30][N:31]([C:33]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:32]=2)=[CH:20][CH:21]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19093674HCID 19093674, compound

Product 1

HCID 19093675HCID 19093675, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 5,7-diethyl-2-oxo-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridin-3-carboxylate (0.41 g) was dissolved in dioxan (5 ml) containing aqueous 1M sodium hydroxide solution (0.55 ml) and the mixture was stirred for 16 hours. Volatile material was removed by evaporation and the residue was partitioned between ethyl acetate and water. The aqueous phase was separated, acidified to pH 4-5 with 1M aqueous citric acid solution and then extracted twice with dichloromethane. The combined extracts were dried (MgSO4) and the solvent was removed by evaporation. The residue was purified by flash chromatography, eluting initially with ethyl acetate/petroleum ether (2:1 v/v), followed by ethyl acetate and then methanol/ethyl acetate (1:9 v/v), to give 5,7-diethyl-2-oxo-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridin-3-carboxylic acid (A) (0.184 g) as a solid; NMR (d6 -DMSO+d4 -acetic acid): 1.15(t,3H), 1.32 (t,3H), 2.68(q,2H), 3.22(q,2H), 5.66(s,2H), 6.8-7.9(complex m,24H), 9.06(s,1H), mass spectrum (+ve FAB, DMSO/NBA): 745(M+H)+ ; microanalysis, found: C, 66.9; H, 5.0; N, 10.0%; C46H38N6O3.1.7SiO2 requires: C, 67.0; H, 4.6; N, 10.2%.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe aqueous phase was separated
  4. extractionextracted twice with dichloromethane
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent was removed by evaporation
  7. customThe residue was purified by flash chromatography
  8. washeluting initially with ethyl acetate/petroleum ether (2:1 v/v)

Sources & evidence

ORD record
ord-20412ae523e94e79ac6504e258682b59
Source dataset
uspto-grants-1993_06
Patent number
US05217976

Reaction notes

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