N-Trityl Losartan Carboxaldehyde → 2-n-Butyl-1-[(2'-(N-triphenylmethyl-tetrazol-5-yl)biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde

HRID 487177Notes

Reaction equation

HRID 487177 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30]([C:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:7]([CH:11]=[O:12])=[C:8](Cl)[N:9]=1)[CH2:2][CH2:3][CH3:4].[H][H].O.O.O.C([O-])(=O)C.[Na+]>CO.[Pd]>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30]([C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:29]=[N:28][N:27]=3)=[CH:18][CH:19]=2)[C:7]([CH:11]=[O:12])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 11657587N-Trityl Losartan CarboxaldehydeHCID 23665404Sodium Acetate TrihydrateHCID 178418361HCID 178418361, compound

Product 1

HCID 190944332-n-Butyl-1-[(2'-(N-triphenylmethyl-tetrazol-5-yl)biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

12.0 g (18.1 mmol) of 2-n-butyl-4-chloro-1-[(2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde in 150 ml of methanol are hydrogenated at 25° C. for 1.5 h at a hydrogen pressure of about 3 bar in the presence of 1. 2 g of palladium on active carbon (5%) and 2.46 g (18.1 mmol) of sodium acetate trihydrate. The solution is then filtered off from the catalyst and concentrated, and the residue is chromatographed on silica gel 60 using ethyl acetate/petroleum ether (1:1).

Workup

  1. filtrationThe solution is then filtered off from the catalyst
  2. concentrationconcentrated
  3. customthe residue is chromatographed on silica gel 60 using ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record
ord-a1365638ccc5488da9b094803df12262
Source dataset
uspto-grants-1994_03
Patent number
US05294633

Reaction notes

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