1,2-Dichloroethane → N-[1-(benzooxazol-2-yl-hydroxy-methyl)-propyl]-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyramide

HRID 1830190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1830190
[CH:1]1([CH2:7][CH:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.OC(C(F)(F)F)=O.[NH2:28][CH:29]([CH2:41][CH3:42])[CH:30]([C:32]1[O:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=1)[OH:31].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[O:33]1[C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=[C:32]1[CH:30]([OH:31])[CH:29]([NH:28][C:9](=[O:11])[CH:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH2:12][C:13]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:41][CH3:42]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 218998342-Cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acidHCID 866023552-amino-1-benzooxazol-2-yl-butan-1-ol TFA salt

Produkt 1

HCID 22054056N-[1-(benzooxazol-2-yl-hydroxy-methyl)-propyl]-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyramideAusbeute 106 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of 2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid (84.9 mg, 0.3 mmol), 2-amino-1-benzooxazol-2-yl-butan-1-ol TFA salt (96.9 mg), prepared as in reference 21, and HOBt (55.1 mg, 0.36 mmol) in MeCl2 (5 ml), was added EDC (86.4 mg, 0.45 mmol) and N-methylmorpholine (0.25 ml) at room temperature. After stirring for 14 hours, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3, brine, dried with MgSO4 and concentrated to yield 150 mg of N-[1-(benzooxazol-2-yl-hydroxy-methyl)-propyl]-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyramide; MS: 470.5(M−1), 472.4(M+1).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-63673715ddb24e04855a6ac3286a5d8a
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064123B1

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