tert-Butanol → HCID 59753641, Verbindung

HRID 751669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751669
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:21][C:22](O)([CH3:24])[CH3:23].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:22]([O:19][C:18](=[O:20])[C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)([CH3:24])([CH3:23])[CH3:21]

Komponenten

6

Edukt 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanine

Produkt 1

HCID 59753641HCID 59753641, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-N-Boc-4-fluorophenylalanine (2.83 g, 10.0 mmol), DMAP (0.12 g, 1.0 mmol) in DCM (20 mL) and 2-methyl-2-propanol (1.05 mL, 11.0 mmol), was added DCC (2.27 g, 11.0 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was filtered and washed several times with DCM. The filtrate was concentrated in vacuo and chromatographed on silica gel eluting with ethyl acetate:isohexane (1:4) to give the title compound. δH (CDCl3): 1.39 (9H, s), 1.41 (9H, s), 3.01 (2H, m), 4.41 (1H, m), 4.98 (1H, m), 6.95 (2H, m), 7.12 (2H, m).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washwashed several times with DCM
  3. concentrationThe filtrate was concentrated in vacuo
  4. customchromatographed on silica gel eluting with ethyl acetate:isohexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-7774d3b13c1046c8a9a9c6c2c7975266
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405210B2

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