1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (4-Nitro-2-phenylbenzoyl)methionine methyl ester

HRID 356086Notes

Reaction equation

HRID 356086 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][CH:14]=2)[CH:5]=1)([O-:3])=[O:2].Cl.[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH2:26][S:27][CH3:28])[NH2:24].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>C(Cl)Cl.CCN(CC)CC>[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH2:26][S:27][CH3:28])[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][CH:14]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 106578414-Nitro-2-phenylbenzoic acidHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 67564255N-BOC-4-aminobenzoyl methionine methyl ester

Product 1

HCID 18666764(4-Nitro-2-phenylbenzoyl)methionine methyl esterYield 85.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-nitro-2-phenylbenzoic acid (0.30 g, 1.23 mmol), methionine methyl ester hydrochloride salt (0.27 g, 1.35 mmol), EDCI (0.26 g, 1.35 mmol), HOBT (0.18 g, 1.35 mmol) and Et3N (0.19 ml) in dry CH2Cl2 (4.9 ml) were reacted according to the above procedure and worked up as described for N-BOC-4-aminobenzoyl methionine methyl ester in Example 1. After recrystallization from ethyl acetate and hexanes, 0.41 g (85.5%) of pure product was isolated. mp 98°-101° C.; 1H NMR (CDCl3) 1.62-1.73 (1 H, m), 1.79-1.88 (1 H, m), 1.91 (3 H, s), 1.99 (2 H, t, J=7.2 Hz), 3.59 (3 H, s), 4.53 (1 H, m), 6.45 (1 H, d, J=7.8 Hz), 7.33-7.40 (5 H, m), 7.67 (1 H, d, J=8.3 Hz), 8.07-8.12 (2 H, m); 13C NMR (CDCl3) 14.92, 29.11, 30.67, 51.51, 52.29, 121.86, 124.74, 128.27, 128.60, 128.69, 129.52, 137.50, 140.56, 141.02, 148.09, 167.23, 171.23; m/ z (FAB) , 389 (M+1).

Workup

  1. customAfter recrystallization from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-64e085cfb6464e6a8fa467b8580836d4
Source dataset
uspto-grants-1998_11
Patent number
US05834434

Reaction notes

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