1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(tert-Butoxycarbonyl-{4-[tert-butoxycarbonyl-(2-octadec-8-enyloxycarbonyl-ethyl)-amino]-butyl}-amino)-propionic acid octadec-8-enyl ester

HRID 31537

Reaktionsgleichung

Reaktionsgleichung von HRID 31537
[C:1]([CH2:6][CH2:7][N:8]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O:3][CH2:4][CH3:5])=[O:2].CN([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40]N=1)C.C(O)C[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]/[CH:52]=[CH:53]\[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61].CCN=C=N[CH2:68][CH2:69][CH2:70]N(C)C>ClCCl>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][CH2:21][N:13]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][N:8]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:7][CH2:6][C:1]([O:3][CH2:4][CH2:5][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH:56]=[CH:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH3:46])=[O:2])[CH2:27][CH2:38][CH2:43][CH2:42][CH2:41][CH2:40][CH:46]=[CH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:70][CH2:69][CH3:68]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 5284499Oleyl AlcoholHCID 86618851N,N'-Bis-(2-carbethoxyethyl)-N,N'-bis-(tert-butoxycarbonyl)-1,4-diaminobutane

Produkt 1

HCID 866188503-(tert-Butoxycarbonyl-{4-[tert-butoxycarbonyl-(2-octadec-8-enyloxycarbonyl-ethyl)-amino]-butyl}-amino)-propionic acid octadec-8-enyl esterAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of the N-protected amino acid 4 (n=4; 15.2 g, 35.1 mmol), dimethylaminopyridine (1.70 g, 14.0 mmol) and oleyl alcohol (18.4 g, 68.4 mmol) in dichloromethane (200 mL) was added a solution of EDCI (13.1 g, 68.4 mmol), in dichloromethane (50 mL) at 0° C. The resulting mixture was allowed to warm to room temperature and then stirred under N2 for 18 h. Dichloromethane (250 mL) was added and the mixture was washed with brine (4×200 mL), dried (Na2SO4) and concentrated in vacuo to leave an oil which was purified by column chromatography eluting with a solvent gradient of CH2Cl2 (50-90%) in hexane to afford the ester 5 as a colourless oil (13.0 g, 40%).

Aufarbeitung

  1. customat 0° C
  2. washthe mixture was washed with brine (4×200 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto leave an oil which
  6. customwas purified by column chromatography
  7. washeluting with a solvent gradient of CH2Cl2 (50-90%) in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4f0683b1699744fda12b8eda8e175f72
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425645B2

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