1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69818591, Verbindung

HRID 2417440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2417440
[CH2:1]([N:8]([C@H:20]([CH2:40][OH:41])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([C:31]2[CH:39]=[CH:38][C:34]([C:35]([OH:37])=O)=[CH:33][CH:32]=2)=[O:30])=[CH:24][CH:23]=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O[N:44]1[C:48]2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.Cl.CN>CN(C)C=O.ClCCCl.C(OCC)(=O)C>[CH2:1]([N:8]([C@H:20]([CH2:40][OH:41])[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:29](=[O:30])[C:31]2[CH:32]=[CH:33][C:34]([C:35]([NH:44][CH3:48])=[O:37])=[CH:38][CH:39]=2)=[CH:26][CH:27]=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6364545Methylamine hydrochlorideHCID 69817718HCID 69817718, Verbindung

Produkt 1

HCID 69818591HCID 69818591, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-[[[4-((2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]phenyl]-amino]carbonyl]benzoic acid (14.6 mg) in N,N-dimethylformamide (200 μl) were added 1.0 M solution of 1-hydroxybenzotriazole hydrate in N,N-dimethylformamide (31.6 μl) and 1.0 M solution of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide in 1,2-dichloroethane (31.6 μl) at room temperature. To the mixture was added methylamine hydrochloride (2.2 mg) and the whole was stirred overnight. The reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml×1) and brine (10 ml×1) successively, dried over magnesium sulfate, and evaporated to give a pale yellow paste. The crude product was purified by a recycling preparative high pressure liquid chromatography equipped with a gel permeation chromatography column (eluent: chloroform) to give N1-[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]-phenyl]-N4-methylterephthalamide (14.0 mg) as a white solid.

Aufarbeitung

  1. washwashed with water (10 ml×1) and brine (10 ml×1) successively
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customto give a pale yellow paste
  5. customThe crude product was purified by a recycling preparative high pressure liquid chromatography
  6. customequipped with a gel permeation chromatography column (eluent: chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-91b1fdc058e54bdda51e7b90653f97c2
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06826033B2

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