Ethanolamine → HCID 71243447, Verbindung

HRID 1774440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774440
[OH:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@:3]1([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.CCN(CC)CC.[NH2:37][CH2:38][CH2:39][OH:40].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)Cl>[OH:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@:3]1([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:37][CH2:38][CH2:39][OH:40])=[O:27])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Komponenten

6

Edukt 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 60155116HCID 60155116, Verbindung

Produkt 1

HCID 71243447HCID 71243447, VerbindungAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(((1R,2R)-1-hydroxy-2,3-dihydro-1H,1′H-[2,2′-biinden]-2-yl)methyl)benzoic acid (100 mg, 0.26 mmol), Et3N (157 mg, 1.56 mmol) and 2-amino ethanol (40 mg, 0.65 mmol) in DCM (5 mL), was added T3P (0.33 mL, 50 wt % solution in ethyl acetate, 0.52 mmol) and then stirred at room temperature for 12 h. The reaction mixture was quenched with water (25 mL) and extracted with DCM (3×25 mL). The organic layer was washed with brine (25 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by CombiFlash using 20% ethyl acetate in chloroform as an eluent to yield 80 mg (72%) of the title compound as an off white solid.

Aufarbeitung

  1. customThe reaction mixture was quenched with water (25 mL)
  2. extractionextracted with DCM (3×25 mL)
  3. washThe organic layer was washed with brine (25 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by CombiFlash

Quellen und Nachweise

ORD-Eintrag
ord-fbcd1f2f1d3e402b8c67ff5d68f65152
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260376B2

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