3-Tert-butyl-1,2-oxazol-5-amine → N-(3-tert-Butyl-isoxazol-5-yl)-4-hydroxy-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-butyramide

HRID 1924866

Reaktionsgleichung

Reaktionsgleichung von HRID 1924866
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Al](C)C.[CH3:15][C:16]1([S:22]([CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)(=[O:24])=[O:23])[CH2:20][CH2:19][O:18][C:17]1=[O:21]>C(Cl)Cl.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:17](=[O:21])[C:16]([CH3:15])([S:22]([CH:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)(=[O:24])=[O:23])[CH2:20][CH2:19][OH:18])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 16682925TrimethylaluminumHCID 582805793-Methyl-3-(tetrahydro-pyran-4-sulfonyl)-dihydro-furan-2-one

Produkt 1

HCID 44609910N-(3-tert-Butyl-isoxazol-5-yl)-4-hydroxy-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-butyramideAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of 3-tert-butyl-isoxazol-5-ylamine (0.421 g; 3.00 mmol) in methylene chloride (10 mL) was added dropwise the trimethylaluminum (1.50 mL of a 2.0 M solution in toluene; 3.0 mmol). The mixture was stirred 15 minutes and 3-methyl-3-(tetrahydro-pyran-4-sulfonyl)-dihydro-furan-2-one (0.596 g; 2.40 mmol) was added. The mixture was heated to 45° C. overnight, cooled to room temperature, carefully quenched with 0.5 mL methanol, applied to a plug of silica gel and eluted with ethyl acetate. Removal of the volatiles in vacuo provided a residue which was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. The product-rich fractions were concentrated in vacuo to provide 0.646 g of the desired product. 1H NMR (CDCl3) δ 9.92 (bs, 1H), 6.29 (s, 1H), 4.11-3.92 (m, 4H), 3.86 (m, 1H), 3.60 (m, 1H), 3.40 (m, 2H), 2.57 (m, 1H), 2.36 (m, 1H), 2.12-1.90 (m, 4H), 1.80 (s, 3H), 1.32 (s, 9H). MS (ESI): m/e 389 (M+H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customcarefully quenched with 0.5 mL methanol
  3. washeluted with ethyl acetate
  4. customRemoval of the volatiles in vacuo
  5. customprovided a residue which
  6. customwas purified by silica gel chromatography
  7. concentrationThe product-rich fractions were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-81e0d7b338aa40ad89fe7838a514abee
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178568B2

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