Sodium Hydroxide → HCID 178447302, 화합물

HRID 12596노트

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HRID 12596 반응식
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]

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 67245353N-(4-iodobenzyl)-N-valeryl-L-valineHCID 178514830HCID 178514830, 화합물

생성물 1

HCID 178447302HCID 178447302, 화합물수율 85.1%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 887Methanol용매HCID 962Water용매

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온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2c34eba3d0b341ddb43c12b392296d96
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728021B2

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