(p-Acetylphenoxy)acetic acid → 3-[2-(4-Acetyl-phenoxy)acetylamino]-benzoic acid methyl ester

HRID 1945377Notes

Reaction equation

HRID 1945377 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:10](=[O:12])[CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:14][CH:13]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 74655(p-Acetylphenoxy)acetic acidHCID 757711-HydroxybenzotriazoleHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 26213993-[2-(4-Acetyl-phenoxy)acetylamino]-benzoic acid methyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 4-acetylphenoxy acetic acid (97 mg, 0.5 mmol) and 3-amino benzoic acid methyl ester (113 mg, 0.75 mmol) in DMF (5.0 mL) were added EDCHCl (144 mg, 0.75 mmol), HOBT (101 mg, 0.75 mmol), and DIPEA (0.13 mL, 0.75 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between Ethyl acetate and brine. The organic phase was dried (anhydrous MgSO4), and concentrated. Purification by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1) gave 3-[2-(4-acetyl-phenoxy)acetylamino]-benzoic acid methyl ester as a white solid (158 mg, 97% yield).

Workup

  1. custompartitioned between Ethyl acetate and brine
  2. dry with materialThe organic phase was dried (anhydrous MgSO4)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1)

Sources & evidence

ORD record
ord-35dc122ed6444705805522cbf0e4f3a8
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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