L-Valine → HCID 178448321, compound

HRID 550046Notes

Reaction equation

HRID 550046 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]2[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=2)=[N:4][N:3]=[N:2]1.[NH2:20][C@H:21]([C:25]([OH:27])=[O:26])[CH:22]([CH3:24])[CH3:23].[OH-].[Na+]>CO.[Pt]>[CH3:23][CH:22]([CH3:24])[C@H:21]([NH:20][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]2[NH:1][N:2]=[N:3][N:4]=2)=[CH:17][CH:16]=1)[C:25]([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 6287L-ValineHCID 14798Sodium HydroxideHCID 1785194042'-(1H-Tetrazol-5-yl)-1,1'-biphenyl-4-carboxaldehyde (Losartan Impurity)

Product 1

HCID 178448321HCID 178448321, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

2′-(1H-tetrazol-5-yl)-biphenyl-4-carbaldehyde (0.79 g; 3.2 mmol) and L-Valine (0.4 g; 3.4 mmol) are suspended in 15 ml methanol. Then sodium hydroxide is added (0.27 g; 6.72 mmol) and the reaction mixture is stirred at room temperature until a clear solution is obtained. 5% Pt/C (15.8 mg; 2 wt/wt-%) is added. The autoclave is sealed and flushed with argon and hydrogen. The pressure is set to 5 bars and the reaction is stirred at 60° C. The reaction completion is monitored by HPLC. Then the autoclave is flushed with argon and the catalyst is filtered off. Further work-up and crystallisation are done similar to example 1 b2).

Workup

  1. customis obtained
  2. customThe autoclave is sealed
  3. customflushed with argon and hydrogen
  4. stirringthe reaction is stirred at 60° C
  5. customThen the autoclave is flushed with argon
  6. filtrationthe catalyst is filtered off
  7. customFurther work-up and crystallisation

Sources & evidence

ORD record
ord-bd173308fa2d4aa7ac708baa0cf6fc05
Source dataset
uspto-grants-2011_05
Patent number
US07943647B2

Reaction notes

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