HCID 178418361, compound → HCID 178447277, compound

HRID 1739087Notes

Reaction equation

HRID 1739087 reaction equation
C([O:8][C:9](=[O:40])[C@H:10]([CH:37]([CH3:39])[CH3:38])[N:11]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:35][N:34]=[N:33][N:32]=2)=[CH:21][C:20]=1[Br:36])[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])C1C=CC=CC=1.[H][H]>O1CCOCC1.[Pd]>[Br:36][C:20]1[CH:21]=[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:35][N:34]=[N:33][N:32]=2)[CH:23]=[CH:24][C:19]=1[CH2:18][N:11]([C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])[C@H:10]([C:9]([OH:40])=[O:8])[CH:37]([CH3:38])[CH3:39]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178447276HCID 178447276, compound

Product 1

HCID 178447277HCID 178447277, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.4 g (4 mmol) of N-[(3-bromo-2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-N-valeryl-(L)-valine benzyl ester in 90 ml of dioxane is hydrogenated at 5 bar and at room temperature with the addition of 1.2 g of Pd/C (10%) until the calculated amount of hydrogen has been absorbed. After evaporation of the filtered solution, the evaporation residue is dissolved in 2N sodium hydroxide solution and extracted with ether, and the aqueous phase is rendered acidic with 2N hydrochloric acid. The title compound is obtained by extracting with ethyl acetate, drying and evaporating as a colourless foam (Rf 0.40, system A2), FAB-MS: m/e=514 (M+H)+.

Workup

  1. customhas been absorbed
  2. customAfter evaporation of the filtered solution
  3. dissolutionthe evaporation residue is dissolved in 2N sodium hydroxide solution
  4. extractionextracted with ether

Sources & evidence

ORD record
ord-ca8fd0e2f3524fa1bb1e324adbf7cd15
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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