m-Phenylenediacetic acid → (3-{[2-(2-Methoxy-phenyl)-ethylcarbamoyl]-methyl}-phenyl)-acetic acid

HRID 553304Notes

Reaction equation

[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)([OH:3])=O.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][NH2:25].ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.Cl.CN(C)CCCN=C=NCC>>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH2:24][NH:25][C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)=[O:3]

Participants

Reactant 5

HCID 29788m-Phenylenediacetic acid

HCID 748962-Methoxyphenethylamine

HCID 757711-Hydroxybenzotriazole

HCID 81531Diisopropylethylamine

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67164052(3-{[2-(2-Methoxy-phenyl)-ethylcarbamoyl]-methyl}-phenyl)-acetic acidYield 30.5%

Procedure

Prepared from (3-carboxymethyl-phenyl)-acetic acid (2.00 g), 2-(2-methoxy-phenyl)-ethylamine (1.60 g), 1-hydroxybenzotriazole (1.40 g), Hunigs base (1.8 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.00 g), using the method of Example 44 (step a), to give 1.03 g of the sub-titled compound as a white solid.

Sources & evidence

ORD record: ord-e5fedfd554524d778c202074a021fdac
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951954B2

Reaction notes

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