Aniline → 2-(6-(Benzyloxy)pyridin-3-yl)-2-(phenylamino)acetic acid

HRID 469489Notes

Reaction equation

HRID 469489 reaction equation
O.O=[CH:3][C:4]([OH:6])=[O:5].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:14]([O:21][C:22]1[N:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[CH2:14]([O:21][C:22]1[N:27]=[CH:26][C:25]([CH:3]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([OH:6])=[O:5])=[CH:24][CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 15620607Glyoxylic acid, monohydrateHCID 177502166-Benzyloxypyridine-3-boronic acid

Product 1

HCID 585570482-(6-(Benzyloxy)pyridin-3-yl)-2-(phenylamino)acetic acidYield 31.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-oxoacetic acid hydrate (0.40 g, 4.37 mmol) and aniline (0.40 ml, 4.37 mmol) in acetonitrile (25 ml), was added 6-(benzyloxy)pyridin-3-ylboronic acid (1.00 g, 4.37 mmol), and the reaction mixture was refluxed for 2 hours. The solvent was evaporated, and the resulting dark brown oil was purified by flash chromatography (DCM/MeOH=97/3) to obtain 2-(6-(benzyloxy)pyridin-3-yl)-2-(phenylamino)acetic acid (460 mg, 31.5% yield).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. customThe solvent was evaporated
  3. customthe resulting dark brown oil was purified by flash chromatography (DCM/MeOH=97/3)

Sources & evidence

ORD record
ord-c67c1db6c20345b9af692cb753f47d3b
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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