m-Phenylenediacetic acid → HCID 67166004, compound

HRID 553303Notes

Reaction equation

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

Participants

Reactant 5

HCID 29788m-Phenylenediacetic acid

HCID 757711-Hydroxybenzotriazole

HCID 812922-Methoxybenzylamine

HCID 81531Diisopropylethylamine

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

Product 1

HCID 67166004HCID 67166004, compoundYield 31%

Procedure

Prepared from 2-methoxy-benzylamine (1.4 g), (3-carboxymethyl-phenyl)-acetic acid (2 g), 1-hydroxybenzotriazole (1.4 g), Hunigs base (1.8 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.0 g), using the method of Example 44 (step a), to give 990 mg of the sub-titled compound as a white solid.

Sources & evidence

ORD record: ord-3992b8cb610b4e719e11e291d02df082
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951954B2

Reaction notes

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