Dicyclohexylcarbodiimide → Methyl (R)-4-[(2-hydroxy-1-phenylethyl)amino]-4-oxo-2-butenoate

HRID 233628

Reaktionsgleichung

Reaktionsgleichung von HRID 233628
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O-:6])=O.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[C:36]1([C@H:42]([CH2:44][OH:45])[NH2:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(OCC)(=O)C>[OH:45][CH2:44][C@H:42]([NH:43][C:4](=[O:6])[CH:3]=[CH:2][C:1]([O:8][CH3:9])=[O:7])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 2724025(R)-beta-aminophenethyl alcoholHCID 27960291-Hydroxybenzotriazole hydrateHCID 21721168(E)-4-methoxy-4-oxobut-2-enoate

Produkt 1

HCID 53871317Methyl (R)-4-[(2-hydroxy-1-phenylethyl)amino]-4-oxo-2-butenoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of monomethyl fumarate (3.0 g, 23 mmol) in ethyl acetate (40 mL) was added 1-hydroxybenzotriazole hydrate (3.0 g, 22 mmol), followed by N,N'-dicyclohexylcarbodiimide (4.5 g, 22 mmol) and the reaction stirred at ambient temperature for 1 hour. The solid was filtered off and discarded. To the filtrate was added (R)-α-phenylglycinol (3.0 g, 22 mmol ) and stirring continued for 20 minutes. The volatiles were removed in vacuo (40° C.) and the residue purified by flash chromatography on normal phase silica gel using hexane: ethyl acetate (1:1) as eluant. Recovered 2.5 g (46%) of (18) as a white solid, m.p. 75°-77° C.; IR (neat) 3250 (OH), 1729 (C=O ester), 1666 (C=O amide), 1640 (C=C)cm-1 ;NMR (CDCl3) δ 7.3-7.4 (5H, m, Ph), 7.0 (1H, d, J 15 Hz, trans alkene), 6.8 (1H, d, J 15 Hz, trans alkene), 6.6 (1H, br d, NH), 5.2 (1H, m, CH), 3.9 (2H, t, J 3 Hz, CH2), 3.8 (3H, s, CH3), 2.3 (1H, t, J 5 Hz, OH); [α]D -53° (CHCl3, 24° C., c=1); anal C13H15NO4 ; requires C 62.64% H 6.07% N 5.62%; found C 62.72% H 5.92% N 5.48%.

Aufarbeitung

  1. filtrationThe solid was filtered off
  2. stirringstirring
  3. waitcontinued for 20 minutes
  4. customThe volatiles were removed in vacuo (40° C.)
  5. customthe residue purified by flash chromatography on normal phase silica gel
  6. customRecovered 2.5 g (46%) of (18) as a white solid, m.p. 75°-77° C.
  7. custom[α]D -53° (CHCl3, 24° C., c=1)

Quellen und Nachweise

ORD-Eintrag
ord-d97dbee2fa244c0bb9d07ea0152a6b60
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05593967

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