1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[4-Nitro-2-(2-methylphenyl)benzoyl]leucine Methyl Ester

HRID 2121262Notes

Reaction equation

HRID 2121262 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:5]=1)([O-:3])=[O:2].[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH2:24].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>>[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:24][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]

Participants

5

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 65105(+)-L-Leucine methyl esterHCID 757711-HydroxybenzotriazoleHCID 234360742-(2-Methylphenyl)-4-nitrobenzoic acid

Product 1

HCID 69892638N-[4-Nitro-2-(2-methylphenyl)benzoyl]leucine Methyl EsterYield 99%

Procedure

4-nitro-2-(2-tolyl)benzoic acid (1.72 g, 6.7 mmol) was coupled with (L)-leucine methyl ester in the presence of EDCI and HOBT to give the desired compound (2.55 g, 99% yield). 1H NMR (CDCl3) δ 8.29 (d, J=8.7 Hz, 1H), 8.10-8.16 (m, 2H), 7.18-7.42 (m, 4H), 5.76 (d, J=7.6 Hz, 1H), 4.49 (br m, 1H), 3.66 (s, 3H), 2.19 (s, 1H), 2.08 (s, 2H), 1.30-1.39 (m, 1H), 1.02-1.09 (m, 2H), 0.75-0.80 (dd, J=6.7 and 7.1 Hz, 6H).

Sources & evidence

ORD record
ord-1604134beda64dd9af67565dd03f4a3d
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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