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

HRID 1739143
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HRID 1739143 반응식
[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>C(Cl)Cl.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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

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 CH2Cl2 (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 (1H, m), 1.85-1.97 (1H, m), 2.01 (3H, s), 2.05 (3H, t, J=7.7 Hz), 2.38 (6H, s), 3.70 (3H, s), 4.67-4.74 (1H, m), 6.03 (1H, d, J=7.9 Hz), 7.05 (2H, s), 7.09 (1H, s), 7.84-7.87 (1H, m), 7.84-7.87 (1H, m), 8.23-8.26 (2H, 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.

후처리

  1. customAfter recrystallization from ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-bb3d2e8fd31f4079999a359ea9bd69fa
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05965539

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