Diisopropyl Ether → HCID 178447302, compound

HRID 2116618Notes

Reaction equation

HRID 2116618 reaction equation
[CH:1]([CH:4]1[C:8](=[O:9])[O:7][CH:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[N:5]1[C:46](=[O:51])[CH2:47][CH2:48][CH2:49][CH3:50])([CH3:3])[CH3:2].C(OC(C)C)(C)C>C1COCC1.[Pd]>[CH3:50][CH2:49][CH2:48][CH2:47][C:46]([N:5]([C@H:4]([C:8]([OH:9])=[O:7])[CH:1]([CH3:3])[CH3:2])[CH2:6][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[NH:23][N:24]=[N:25][N:26]=2)=[CH:14][CH:15]=1)=[O:51]

Participants

5

Reactant 2

HCID 7914Diisopropyl EtherHCID 23073590HCID 23073590, compound

Product 1

HCID 178447302HCID 178447302, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 4-isopropyl-3-pentanoyl-2-[2′-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-yl]oxazolidin-5-one (1.0 g, 1.5 mmoles) in 20 ml of THF is hydrogenated under 5 bars, at 60° C., in the presence of Pd(5%)/C (100 mg). After completion of the reaction, the mixture is cooled and the catalyst is filtered off. After working up the reaction mixture as in Example 4, valsartan (0.33 g, molar yield: 53%) is isolated by crystallization from isopropyl ether.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe mixture is cooled
  3. filtrationthe catalyst is filtered off

Sources & evidence

ORD record
ord-d7e6f376f38d4776a9a3bead17913648
Source dataset
uspto-grants-2008_10
Patent number
US07439261B2

Reaction notes

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