Trifluoroacetic acid → Methyl-phenyl-carbamic Acid 4-[2-(2-dimethylamino-acetylamino)-ethyl]-phenyl Ester

HRID 1180039Notes

Reaction equation

HRID 1180039 reaction equation
CCN=C=NC[CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].C(N(CC)CC)C.[NH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29](=[O:38])[N:30]([CH3:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:24][CH:23]=1.C(O)(C(F)(F)F)=[O:40]>C(Cl)Cl>[CH3:10][N:9]([CH3:11])[CH2:8][C:7]([NH:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29](=[O:38])[N:30]([CH3:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:26][CH:27]=1)=[O:40]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69520583Methyl-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl Ester

Product 1

HCID 69517500Methyl-phenyl-carbamic Acid 4-[2-(2-dimethylamino-acetylamino)-ethyl]-phenyl EsterYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N,N-dimethylglycine, HCl (0.3 mmol), EDAC (0.36 mmol) and triethylamine (1.0 mmol) in CH2Cl2 (10 mL) was added N-hydroxybenzoetriazole and N-methyl-N-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl ester as its TFA salt (0.3 mmol). The mixture was stirred 16 h at rt and purified by preparative HPLC (Gilson) to give the title compound in 66% yield as an oil.

Workup

  1. custompurified by preparative HPLC (Gilson)

Sources & evidence

ORD record
ord-ac67599388bf40d58d03d18849065339
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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