Benzylamine → (3R)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide

HRID 419385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419385
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:6]([C:15]([OH:17])=O)[CH2:5][O:4][CH2:3]1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[CH2:35]([NH2:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:6]([C:15]([NH:42][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:17])[CH2:5][O:4][CH2:3]1

Komponenten

7

Edukt 5

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13543371(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid

Produkt 1

HCID 59452664(3R)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(3R)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (3.67 g, 15.6 mmol) and 1-hydroxybenzotriazole (2.53 g, 18.7 mmol) in DCM (50 mL) cooled to 0° C. N-Methylmorpholine (8.50 mL, 77.3 mmol), benzylamine (1.87 mL, 17.2 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.26 g, 17.2 mmol) added sequentially. The reaction was stirred at rt overnight, washed with H2O (50 mL), 6N HCl (30 mL), H2O (50 mL) and dried over MgSO4 to provide the title compound of step C (5.09 g, 15.6 mmol, 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.59 (d, J=15.2 Hz, 1H), 3.82 (t, J=2.9 Hz, 1H), 3.86-3.97 (m, 2H), 4.07-4.17 (m, 2H), 4.23-4.34 (m, 2H), 5.30 (d, J=15.4 Hz, 1H), 7.17-7.22 (m, 5H), 7.24-7.32 (m, 5H), 8.60 (t, J=5.6 Hz, 1H).

Aufarbeitung

  1. washwashed with H2O (50 mL), 6N HCl (30 mL), H2O (50 mL)
  2. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-ff0507a7b19f431ba85fd0cfdd1636b1
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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