Actarit → Boc-aminopropanol actarit

HRID 1359990

Reaktionsgleichung

Reaktionsgleichung von HRID 1359990
[C:1]([O:5][C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.[CH3:18][C:19]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][C:29]([OH:31])=[O:30])=[CH:26][CH:27]=1)=[O:20].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:6]([C:8]([NH2:12])([OH:11])[CH2:9][CH3:10])([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7].[CH3:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([OH:31])=[O:30])=[CH:24][CH:23]=1)=[O:20]

Komponenten

8

Edukt 4

HCID 2018ActaritHCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23149331t-Butoxycarbonyl-aminopropanol

Produkt 1

HCID 86623043Boc-aminopropanol actaritAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 2 ml of dichloromethane, 123.1 mg (0.703 mmol) of the Boc-aminopropanol obtained in Reference Example 1 was dissolved, and then a DMF solution (1 ml) of 136.0 mg (0.704 mmol) of actarit was added thereto, and 17.1 mg (0.140 mmol) of DMAP and 175.4 mg (0.915 mmol) of WSCI.HCl were added thereto in this order under ice-cooling, followed by stirring overnight while gradually returning to room temperature. Ethyl acetate was added thereto, followed by separation by washing with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively. After dehydration drying with sodium sulfate, ethyl acetate was evaporated under reduced pressure. The precipitate was purified by silica gel column chromatography to give 203.1 mg (83%) of the titled compound. The structure was identified by 1H-NMR.

Aufarbeitung

  1. dissolutionwas dissolved
  2. temperaturein this order under ice-cooling
  3. customwhile gradually returning to room temperature
  4. customfollowed by separation
  5. washby washing with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively
  6. dry with materialAfter dehydration drying with sodium sulfate, ethyl acetate
  7. customwas evaporated under reduced pressure
  8. customThe precipitate was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-31cb5099ca0740c893807ef3f604837f
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879817B2

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