1,2-Dichloroethane → (1S,2S)-2-(3-oxaheptanoyl)amino-3-morpholino-1-phenyl-1-propanol

HRID 2186657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2186657
[C:1]([OH:9])(=O)[CH2:2][O:3][CH2:4][CH2:5][CH2:6][CH3:7].C(N(CC)CC)C.C(Cl)CCl.[NH2:21][C@@H:22]([CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)[C@H:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[OH:24]>C(Cl)Cl>[C:1]([NH:21][C@@H:22]([CH2:31][N:32]1[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1)[C@H:23]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[OH:24])(=[O:9])[CH2:2][O:3][CH2:4][CH2:5][CH2:6][CH3:7]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 41958Butoxyacetic acidHCID 10513992(1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanol

Produkt 1

HCID 69821554(1S,2S)-2-(3-oxaheptanoyl)amino-3-morpholino-1-phenyl-1-propanolAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methylene chloride (20 ml), 3-oxaheptanoic acid (529.0 mg, 4.0 mmol), triethylamine (1.40 ml, 10.0 mmol) and EDC (1.15 g, 6.0 mmol) were added to (1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanol (944.0 mg, 4.0 mmol), followed by stirring overnight. Methylene chloride (100 ml) was added to the reaction solution. After washed with a saturated sodium hydrogen carbonate solution (50 ml), water (50 ml) and saturated brine (50 ml) successively, the organic layer was dried over sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform:ethanol=30:1) to obtain the title compound (825 mg, yield 59%) as colorless oil.

Aufarbeitung

  1. washAfter washed with a saturated sodium hydrogen carbonate solution (50 ml), water (50 ml) and saturated brine (50 ml) successively
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (chloroform:ethanol=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-88b2430ffa324b0a8eb69f824dba3c67
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06407064B2

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