Sodium Hydroxide → HCID 178447302、化合物

HRID 12596ノート

反応式

HRID 12596 の反応式
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]

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 67245353N-(4-iodobenzyl)-N-valeryl-L-valineHCID 178514830HCID 178514830、化合物

生成物 1

HCID 178447302HCID 178447302、化合物収率 85.1%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2c34eba3d0b341ddb43c12b392296d96
出典データセット
uspto-grants-2010_06
特許番号
US07728021B2

反応ノート

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