1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22557098, Verbindung

HRID 583847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583847
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9]([O:13][C:14]([N:16](C)[C@H:17]([C:19]([OH:21])=O)[CH3:18])=[O:15])([CH3:12])([CH3:11])[CH3:10].[CH3:23]N(C)CCCN=C=NCC>ClCCl>[O:8]=[C:3]1[CH2:4][CH2:5][C:6](=[O:7])[N:2]1[O:1][C:19](=[O:21])[C:17]([NH:16][C:14]([O:13][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:15])([CH3:18])[CH3:23]

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid

Produkt 1

HCID 22557098HCID 22557098, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred solution of N-hydroxysuccinimide (112 g, 0.973 mol), N-t-butoxycarbonyl-methylalanine (197 g, 0.969 mol), and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide (186 g, 0.970 mol) in anhydrous dichloromethane (1.4 L) was stirred at room temperature for about 18 hours under nitrogen atmosphere. The reaction mixture was washed three times each with saturated sodium bicarbonate solution and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound of part 1-D as a white solid (256 g, 88%): PBMS (M+18)+ 318; 1H NMR=250 MHz (CDCl3) δ: 4.91 (NH, br s, 1H), 2.84 (—CO(CH2)2CO—, s, 4H), 1.67 (Me, s, 6H), 1.48 (BOC, s, 9H).

Aufarbeitung

  1. washThe reaction mixture was washed three times each with saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-98d739651e08401f854e2f4f47e2ac04
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924280B2

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