Acetic Anhydride → Ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)hex-5-enoate

HRID 579513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 579513
[C:1]([O:5][C:6]([NH:8][C:9]([CH2:19][OH:20])([CH2:15][CH2:16][CH:17]=[CH2:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C1C=CC=CN=1)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>ClCCl>[C:30]([O:20][CH2:19][C:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])([CH2:15][CH2:16][CH:17]=[CH2:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:32])[CH3:31]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 71579992Ethyl 2-(tert-butoxycarbonylamino)-2-(hydroxymethyl)hex-5-enoate

Produkt 1

HCID 86663718Ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)hex-5-enoateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of the ethyl 2-(tert-butoxycarbonylamino)-2-(hydroxymethyl)hex-5-enoate (10.0 g, 35 mmol) and dimethylaminopyridine (4.48 g, 35 mmol) in dichloromethane (100 mL) was treated with acetic anhydride and stirred at room temperature overnight. The solution was concentrated and the resulting residue purified using a combiflash system (89 g column, eluting with 20-50% ethyl acetate in heptanes) to give ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)hex-5-enoate (10 g, 80%). 1H NMR (CDCl3) δ 5.78-5.68 (m, 1H), 5.55 (bs, 1H), 5.03-4.93 (m, 2H), 4.73 (d, J=11.0 Hz, 1H) 4.32 (d, J=11.0 Hz, 1H,), 4.20 (q, J=7.2 Hz, 2H), 2.36 (m, 1H), 2.07-2.05 (m, 1H), 2.02 (s, 3H), 1.89-1.75 (m, 2H), 1.43 (m, 9H), 1.27 (t, J=7.2 Hz, 3H). MS found for C16H27NO6 m/z[330(M+1)].

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. customthe resulting residue purified
  3. washa combiflash system (89 g column, eluting with 20-50% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-c7b5c4fee8504f0bb54ff0519a0cda7f
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040703B2

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