Tetrahydrofuran → 3-[(4-Methylamino-3-nitro-benzoyl)-phenyl-amino]propionic acid methyl ester

HRID 449739Notes

Reaction equation

HRID 449739 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[CH3:15][O:16][C:17](=[O:27])[CH2:18][CH2:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O1CCCC1>>[CH3:15][O:16][C:17](=[O:27])[CH2:18][CH2:19][N:20]([C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([NH:2][CH3:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 89103N-Phenyl-beta-alanine methyl esterHCID 179464494-(Methylamino)-3-nitrobenzoyl chloride

Product 1

HCID 580694213-[(4-Methylamino-3-nitro-benzoyl)-phenyl-amino]propionic acid methyl ester

Procedure

To a solution of 4-methylamino-3-nitro-benzoic acid chloride (23.3 mmol) and 3-phenylamino-propionic acid methyl ester (23.3 mmol) in 80 mL dry tetrahydrofuran (THF) triethylamine (50.2 mmol) was added dropwise under stirring at room temperature. After three hours the reaction mixture was evaporated to dryness, the remaining solid triturated with water and the solid product isolated through filtration.

Workup

  1. customAfter three hours the reaction mixture was evaporated to dryness
  2. customthe remaining solid triturated with water
  3. customthe solid product isolated through filtration

Sources & evidence

ORD record
ord-423a64f494b3413189d10eaba01d5713
Source dataset
uspto-grants-2013_07
Patent number
US08486398B2

Reaction notes

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