p-Toluenesulfonyl azide → Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-diazo-acetate

HRID 524410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524410
[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:9]1[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([N:38]=[N+:39]=[N-])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[C:9]1[S:10][CH:11]=[C:12]([C:14](=[N+:38]=[N-:39])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 13661p-Toluenesulfonyl azideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67376904Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]acetate

Produkt 1

HCID 86669544Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-diazo-acetateAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]acetate (synthesized as per preparation 44; 3.8 g, 9.35 mmol) in dry acetonitrile was added para-toluene sulfonyl azide (2.04 g, 10.3 mmol) followed by DBU (2.09 mL, 14.0 mmol) in dropwise manner. The reaction stirred for 30 min. then poured in ice cold water (20 mL) extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide crude product, which was purified by column chromatography using 5-7% ethyl acetate in hexane to afford Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-diazo-acetate (3.3 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto provide crude product, which
  6. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b20995f64fb84dfe9fbaf92016e5ee14
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340506B2

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