Dimethylformamide → 4-(Nitrooxy)butyl 2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate

HRID 1425685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425685
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C)C=O.[N+:26]([O-:34])([O:28][CH2:29][CH2:30][CH2:31][CH2:32]Br)=[O:27]>ClCCl>[C:4]([O:3][C:1]([NH:8][CH:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[C:18]([O:20][CH2:32][CH2:31][CH2:30][CH2:29][O:28][N+:26]([O-:34])=[O:27])=[O:19])=[O:2])([CH3:5])([CH3:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 104202524-Bromobutyl nitrate

Produkt 1

HCID 592749814-(Nitrooxy)butyl 2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanoateAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of Boc-(L)-tyrosine (5.0 g, 17.77 mmol) in N,N-dimethylformamide (40 ml) cesium carbonate (5.79 g, 17.77 mmol) was added. The reaction was cooled at 0° C. and a solution of 4-bromobutyl nitrate (17.77 mmol) in dichloromethane (20% w/w, 17.06 g) was added drop wise. The reaction was stirred at 0° C. for 20 minutes and then at room temperature for 22 hours. The mixture was poured into a 5% aqueous NaH2PO4 solution and extracted with diethyl ether (40×4 ml), the organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography, (Biotage System, column FLASH 65+M™ KP-Sil, eluent: gradient n-hexane/ethyl acetate 9/1 (500 ml), to n-hexane/ethyl acetate 1/1 during 4000 ml, n-hexane/ethyl acetate 1/1 (1000 ml)). The product (3.91 g) was obtained.

Aufarbeitung

  1. waitat room temperature for 22 hours
  2. extractionextracted with diethyl ether (40×4 ml)
  3. dry with materialthe organic layers were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography, (Biotage System, column FLASH 65+M™ KP-Sil, eluent: gradient n-hexane/ethyl acetate 9/1 (500 ml), to n-hexane/ethyl acetate 1/1 during 4000 ml, n-hexane/ethyl acetate 1/1 (1000 ml))

Quellen und Nachweise

ORD-Eintrag
ord-ea7c4320a7824a6f9e51da66fe5cc589
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933062B2

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