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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Nitro-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester

HRID 356092
Notes
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Reaction equation

HRID 356092 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]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=2)[CH:5]=1)([O-:3])=[O:2].Cl.[CH3:22][O:23][C:24](=[O:31])[C@H:25]([CH2:27][CH2:28][S:29][CH3:30])[NH2:26].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.COC(=O)[C@H](CCSC)N(C(=O)C1C=CC(N)=CC=1)C(OC(C)(C)C)=O>ClCl.CCN(CC)CC>[CH3:22][O:23][C:24](=[O:31])[C@H:25]([CH2:27][CH2:28][S:29][CH3:30])[NH:26][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]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 234362252-(3,5-Dimethylphenyl)-4-nitrobenzoic acidHCID 67564255N-BOC-4-aminobenzoyl methionine methyl ester

Product 1

HCID 18666763
4-Nitro-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester
Yield 58.4%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 24526ChlorineSolvent

Procedure

4-nitro-2-(3,5-dimethylphenyl)benzoic acid (0.15 g, 0.55 mmol), methionine methyl ester hydrochloride salt (0.11 g, 0.55 mmol), EDCI (0.11 g, 0.55 mmol), HOBT (0.07 g, 0.55 mmol) and Et3N (0.08 ml) in dry CH2 Cl2 (2.2 ml) were reacted and worked up according to the procedure for N-BOC-4-aminobenzoyl methionine methyl ester in Example 1. After recrystallization from ethyl acetate and hexanes, 0.13 g (58.4%) of pure product was isolated. mp 122-124° C.; 1H NMR (CDCl3) 1.2-1.84 (1 H, m), 1.85-1.97 (1 H, m), 2.01 (3 H, s), 2.05 (3 H, t, J=7.7 Hz), 2.38 (6 H, s), 3.70 (3 H, s), 4.67-4.74 (1 H, m), 6.03 (1 H, d, J=7.9 Hz), 7.05 (2 H, s), 7.09 (1 H, s), 7.84-7.87 (1 H, m), 7.84-7.87 (1 H, m), 8.23-8.26 (2 H, m); 13C NMR (CDCl3), 15.20, 21.26, 29.22, 31.15, 51.79, 52.57, 122.07, 25.11, 126.27, 130.03, 130.53, 137.77, 138.82, 140.29, 141.56, 148.41, 167.14, 171.53.

Workup

  1. customAfter recrystallization from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-6d1ea315aa784d9c8bcb91e6fb721667
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05834434

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes