2-(3-Amino-2-hydroxyphenyl)acetic acid → (2-Pentyl-benzoxazol-5-yl)-acetic acid

HRID 1170414Notes

Reaction equation

HRID 1170414 reaction equation
[NH2:1][C:2]1[C:3](O)=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.C([O:16][C:17](=N)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])C>CO>[CH2:18]([C:17]1[O:16][C:7]2[CH:6]=[CH:5][C:4]([CH2:8][C:9]([OH:11])=[O:10])=[CH:3][C:2]=2[N:1]=1)[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 177635762-(3-Amino-2-hydroxyphenyl)acetic acidHCID 18950931Ethyl hexanimidate hydrochloride

Product 1

HCID 68767623(2-Pentyl-benzoxazol-5-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3-aminohydroxy-phenyl)-acetic acid (4.65 g, 27.8 mmol) in methanol (79 ml) was treated with hexanimidic acid ethyl ester hydrochloride (5.00 g, 27.8 mmol) and stirred for 14 hours at RT. The solvent was evaporated in vacuum and the residue purified by silica gel chromatography (eluent: DCM/methanol 10/1). Crystallization from Cyclohexane/n-pentane provided the title compound as colorless crystals. mp: 58.2/57.1° C.

Workup

  1. customThe solvent was evaporated in vacuum
  2. customthe residue purified by silica gel chromatography (eluent: DCM/methanol 10/1)
  3. customCrystallization from Cyclohexane/n-pentane

Sources & evidence

ORD record
ord-b87e68afe0d9417c844da0d505ae2218
Source dataset
uspto-grants-2010_11
Patent number
US07825260B2

Reaction notes

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