Sodium Hydroxide → HCID 178447302, compound

HRID 12596Notes

Reaction equation

HRID 12596 reaction equation
I[C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])[C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[NH:23]1[C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2B(O)O)=[N:26][N:25]=[N:24]1.[OH-].[Na+]>CO.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:19][CH2:18][CH2:17][CH2:16][C:15]([N:7]([C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:27]2[NH:23][N:24]=[N:25][N:26]=2)=[CH:22][CH:21]=1)=[O:20]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 67245353HCID 67245353, compoundHCID 178514830HCID 178514830, compound

Product 1

HCID 178447302HCID 178447302, compoundYield 85.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Nitrogen is bubbled for 5 min. To a mixture made up of 0.20 g (0.48 mmol) of N-(4-iodobenzyl)-N-valeryl-L-valine, 0.115 g (0.61 mmol) of 2-(1H-tetrazol-5-yl)phenylboronic acid, 0.017 g (0.024 mmol) of bis(triphenylphosphine)palladium chloride and 0.115 g (2.87 mmol) of NaOH in 2.4 mL of methanol and 0.7 mL of water are added. The reaction is heated to 70° C. under nitrogen atmosphere. Once 3 h has elapsed the reaction is considered to be completed and the methanol is distilled. The crude product is treated with 25 mL of HCl 1N and 25 mL of AcOEt. The AcOEt phase is dried with anhydrous sodium sulphate and after distilling the solvent the crude product obtained is purified by silica gel chromatography (eluent AcOEt/heptane/AcOH 1.5:5:0.2) to provide 0.178 g (85%) of Valsartan.

Workup

  1. customNitrogen is bubbled for 5 min
  2. additionare added
  3. customOnce 3 h
  4. distillationthe methanol is distilled
  5. additionThe crude product is treated with 25 mL of HCl 1N and 25 mL of AcOEt
  6. dry with materialThe AcOEt phase is dried with anhydrous sodium sulphate
  7. distillationafter distilling the solvent the crude product
  8. customobtained
  9. customis purified by silica gel chromatography (eluent AcOEt/heptane/AcOH 1.5:5:0.2)

Sources & evidence

ORD record
ord-2c34eba3d0b341ddb43c12b392296d96
Source dataset
uspto-grants-2010_06
Patent number
US07728021B2

Reaction notes

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