3-Isoxazolamine, 5-(1,1-dimethylethyl)- → N-(5-tert-butyl-isoxazol-3-yl)-2-(4-chlorobenzenesulfonyl)-4-hydroxy-2-methyl-butyramide

HRID 1924861

Reaktionsgleichung

Reaktionsgleichung von HRID 1924861
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH2:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Al](C)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([C:25]2([CH3:31])[CH2:29][CH2:28][O:27][C:26]2=[O:30])(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl.C1(C)C=CC=CC=1>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:26](=[O:30])[C:25]([S:22]([C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=2)(=[O:24])=[O:23])([CH3:31])[CH2:29][CH2:28][OH:27])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 16682925TrimethylaluminumHCID 582805743-(4-Chloro-benzenesulfonyl)-3-methyl-dihydrofuran-2-one

Produkt 1

HCID 58280577N-(5-tert-butyl-isoxazol-3-yl)-2-(4-chlorobenzenesulfonyl)-4-hydroxy-2-methyl-butyramideAusbeute 4,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-tert-butyl-isoxazol-3-ylamine (0.280 g; 2.00 mmol) in methylene chloride (5 mL) was added dropwise trimethylaluminum (1.0 mL of a 2.0 M solution in toluene; 2.00 mmol). The mixture was stirred 15 minutes and 3-(4-chloro-benzenesulfonyl)-3-methyl-dihydrofuran-2-one (0.440 g; 1.60 mmol) added. The mixture was stirred 18 hours and carefully quenched with 10% aqueous citric acid, aqueous sodium tartrate and chloroform. The organic layer was dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. Removal of the volatiles from the product-rich fractions provided 0.030 g of the desired product. 1H NMR (CDCl3) δ 9.4 (bs, 1H), 7.76 (d, 2H), 7.52 (d, 2H), 6.49 (s, 1H), 3.90 (m, 1H), 3.82 (m, 1H), 2.58 (m, 1H), 2.25 (m, 1H), 1.65 (s, 3H), 1.3 (s, 9H). MS (ESI): m/e 415, 417 (M+H).

Aufarbeitung

  1. stirringThe mixture was stirred 18 hours
  2. customcarefully quenched with 10% aqueous citric acid, aqueous sodium tartrate and chloroform
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customRemoval of the volatiles in vacuo
  5. customprovided a residue which
  6. customwas purified by silica gel chromatography
  7. customRemoval of the volatiles from the product-rich fractions

Quellen und Nachweise

ORD-Eintrag
ord-4a62995fad8849d09f22faeb6b244bd4
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178568B2

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