Methanol → 3-(4-{1-[2-(Hydroxyimino-methyl)-4'-isopropyl-biphenyl-4-yloxy]-3-methyl-butyl}-benzoylamino)-propionic acid methyl ester

HRID 1160920Notes

Reaction equation

HRID 1160920 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH:10]([C:15]2[CH:28]=[CH:27][C:18]([C:19]([NH:21][CH2:22][CH2:23][C:24](O)=[O:25])=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH:12]([CH3:14])[CH3:13])[CH:6]=[CH:5][C:4]=1[C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][CH:30]=1)=O.Cl.[NH2:39][OH:40].[CH3:41][OH:42]>C(OCC)(=O)C>[CH3:41][O:42][C:24](=[O:25])[CH2:23][CH2:22][NH:21][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([CH:10]([O:9][C:7]2[CH:6]=[CH:5][C:4]([C:29]3[CH:30]=[CH:31][C:32]([CH:35]([CH3:36])[CH3:37])=[CH:33][CH:34]=3)=[C:3]([CH:1]=[N:39][OH:40])[CH:8]=2)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 595181533-{4-[1-(2-Formyl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid

Product 1

HCID 866159873-(4-{1-[2-(Hydroxyimino-methyl)-4'-isopropyl-biphenyl-4-yloxy]-3-methyl-butyl}-benzoylamino)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 3-{4-[1-(2-formyl-4′-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid (75 mg, 0.15 mmol) in methanol (10 ml) is added hydroxylamine hydrochloride (104 mg, 1.5 mmol). After 4 h, the mixture is diluted with ethyl acetate, washed with 1N HCl, water, brine, dried over MgSO4, and concentrated. The residue is purified by column chromatography to afford 38 mg of 3-(4-{1-[2-(hydroxyimino-methyl)-4′-isopropyl-biphenyl-4-yloxy]-3-methyl-butyl}-benzoylamino)-propionic acid methyl ester, which is hydrolyzed by 5N NaOH to afford the titled compound (36 mg). MS (ES): 517.2 [M+H]+.

Workup

  1. washwashed with 1N HCl, water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-900fed15a3ca45cfb1e57f5919919780
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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