1,2-Dichloroethane → Methyl (2S)-2-{5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfanylbutyrate

HRID 1251906

Reaktionsgleichung

Reaktionsgleichung von HRID 1251906
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH:8]([C:28]2[S:29][CH:30]=[CH:31][N:32]=2)[O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[C:14]([CH:18]=2)[C:15](O)=[O:16])[CH:6]=1.Cl.[CH3:34][O:35][C:36](=[O:43])[C@H:37]([CH2:39][CH2:40][S:41][CH3:42])[NH2:38].C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH:8]([C:28]2[S:29][CH:30]=[CH:31][N:32]=2)[O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[C:14]([CH:18]=2)[C:15]([NH:38][C@@H:37]([CH2:39][CH2:40][S:41][CH3:42])[C:36]([O:35][CH3:34])=[O:43])=[O:16])[CH:6]=1

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 183244045-[2-(4-Methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoic acid

Produkt 1

HCID 57103056Methyl (2S)-2-{5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfanylbutyrateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoic acid (0.4 g; 0.89 mM), L-methionine methyl ester hydrochloride (0.27 g, 1.35 mM) and DMAP (0.54 g, 4.43 mM) was stirred until solution and EDC (0.026 g, 1.35 mM) in dichloromethane was added and the mixture stirred for 18 hours. It was purified on silica using dichloromethane then methanol/dichloromethane (5:95) as eluant to give the title product (0.47 g, 89%) as a foam.

Aufarbeitung

  1. additionwas added
  2. customIt was purified on silica

Quellen und Nachweise

ORD-Eintrag
ord-f05c14b1537548a2812f9550e8bcb5f6
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342765B1

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