2,4-Dichlorophenylacetic acid → 3-[2-(2,4-Dichloro-phenyl)-acetylamino]-4-methoxy-benzoic acid methyl ester

HRID 1831786

Reaction equation

HRID 1831786 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([NH2:12])[CH:5]=1.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH2:22][C:23](O)=[O:24].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl.CCN(CC)CC.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([NH:12][C:23](=[O:24])[CH2:22][C:16]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=2[Cl:14])[CH:5]=1

Participants

7

Reactant 3

HCID 882092,4-Dichlorophenylacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 2734814Methyl 3-Amino-4-methoxybenzoate

Product 1

HCID 696522653-[2-(2,4-Dichloro-phenyl)-acetylamino]-4-methoxy-benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1.1 g 3-Amino-4-methoxy-benzoic acid methyl ester and 1 g (2,4-Dichloro-phenyl)-acetic acid in 15 ml CH2Cl2, 2.7 ml NEt3 and 1.24 g BOP-Cl and 10 mg DMAP were added. After stirring over night the solvent was removed under reduced pressure and the residue directly purified by chromatography on silica with ethyl acetate/heptane 1:5->1:1 to yield the ester as a yellow oil.

Workup

  1. customwas removed under reduced pressure
  2. customthe residue directly purified by chromatography on silica with ethyl acetate/heptane 1:5->1:1

Sources & evidence

ORD record
ord-0bd7710438bd498597c43962beb16f26
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Linked notes

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