Toluene → [1-(5-Tert-butyl-isoxazol-3-ylcarbamoyl)butyl]-carbamic acid tert-butyl ester

HRID 1294824

Reaktionsgleichung

Reaktionsgleichung von HRID 1294824
Cl.[C:2]([C:6]1[O:10][N:9]=[C:8]([NH2:11])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].C1(C)C=CC=CC=1.C[O:20][C:21](=O)[CH:22]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:24][CH3:25]>C1COCC1>[C:30]([O:29][C:27](=[O:28])[NH:26][CH:22]([C:21](=[O:20])[NH:11][C:8]1[CH:7]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[O:10][N:9]=1)[CH2:23][CH2:24][CH3:25])([CH3:31])([CH3:32])[CH3:33]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 119695193-Isoxazolamine, 5-(1,1-dimethylethyl)-, hydrochloride (1:1)HCID 232782002-Tert-butoxycarbonylamino-pentanoic acid methyl ester

Produkt 1

HCID 69419406[1-(5-Tert-butyl-isoxazol-3-ylcarbamoyl)butyl]-carbamic acid tert-butyl esterAusbeute 141,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 5-tert-butyl-isoxazol-3-ylamine hydrochloride (1.22 g, 8.69 mmol) in THF was added 2 M AIMe3 in toluene (4.3 ml, 8.6 mmol) at room temperature and stirred for 1 hr. A solution of 2-tert-butoxycarbonylamino-pentanoic acid methyl ester (1.005 g, 4.34 mmol) in THF was added and the resulting mixture was stirred at room temperature over the weekend. The mixture was quenched with Rochelle salt and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give 2.08 g of the title compound as a crude oil. The oil was purified by silica gel column chromatography using 1% methanl in methylenechloride as eluent to give the title compound as a white solid (0.554 g). 1H NMR (CDCl3) □ 8.8 (brs, 1H), 6.7 (s, 1H), 4.85 (brs, 1H), 4.22 (m, 1H), 1.9 (m, 1H), 1.4-1.7 (m, 3H), 1.45 (s, 9H), 1.44 (s, 9H), 0.97 (t, 3H) ppm. LC-MS M+1=340.3.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature over the weekend
  2. customThe mixture was quenched with Rochelle salt
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9c63790266c841a5a98ec1b18deb6e63
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241786B2

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