Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate

HRID 529548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529548
O=[CH:2][CH2:3][C@H:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:5].[C:14]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH2:17][CH3:18])=[O:15]>C1COCC1>[C:9]([O:8][C:7]([NH:6][C@H:4]([CH3:5])[CH2:3]/[CH:2]=[CH:19]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:13])([CH3:12])([CH3:11])[CH3:10]

Komponenten

4

Edukt 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 25231755tert-butyl N-[(2R)-4-oxobutan-2-yl]carbamate

Produkt 1

HCID 86706226(R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoateAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (R)-tert-butyl 4-oxobutan-2-ylcarbamate (1.54 g, 8.22 mmol) in THF (25 mL) at rt was added (carbethoxymethylene)triphenylphosphorane (6.30 g, 18.1 mmol) in portions. The resulting clear solution was stirred at rt under argon for 3 days. The reaction mixture was concentrated and the oily residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-60% EtOAc/Hex to give (R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate (1.70 g, 6.61 mmol, 80% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 6.91 (dt, J=15.3, 7.5 Hz, 1H), 5.92-5.82 (m, 1H), 4.37 (s, 1H), 4.19 (q, J=7.1 Hz, 2H), 3.83 (s, 1H), 2.37 (t, J=6.6 Hz, 2H), 1.44 (s, 9H), 1.29 (t, J=7.1 Hz, 3H), 1.15 (d, J=6.7 Hz, 3H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe oily residue was purified
  3. washeluting with a gradient of 0-60% EtOAc/Hex

Quellen und Nachweise

ORD-Eintrag
ord-a199d04452e44054a22ecb80c731ccf8
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346852B2

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