Lithium diisopropylamide → (2S)-2-(N-(2-Azido-benzoyl)-N-formylamino)-propionic acid tert-butyl ester

HRID 602928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602928
[C:1]([O:5][C:6](=[O:12])[C@@H:7]([NH:9][CH:10]=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.[N:21]([C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27])=[N+:22]=[N-:23]>C1COCC1>[C:1]([O:5][C:6](=[O:12])[C@@H:7]([N:9]([C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=1[N:21]=[N+:22]=[N-:23])[CH:10]=[O:11])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 2724682Lithium diisopropylamideHCID 117452552-Azidobenzoyl chlorideHCID 79006784(2S)-2-formylamino-propionic acid tert-butyl ester

Produkt 1

HCID 86630400(2S)-2-(N-(2-Azido-benzoyl)-N-formylamino)-propionic acid tert-butyl esterAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A stirred solution of (2S)-2-formylamino-propionic acid tert-butyl ester (3.524 g, 20.3 mmol) in anhydrous THF (50 mL) was treated at −78° C. with LDA (20.3 mmol) and the reaction was stirred for 15 min. A solution of 2-azidobenzoyl chloride (T. Okawa, T. Sugimori, S. Eguchi and A. Kakehi, Heterocycles, 1998, 47, 1, 375-382) (20.6 mmol) in anhydrous THF (20 mL) was then added dropwise and the reaction mixture was stirred at −78° C. for 1 h before being quenched with saturated aq. NH4Cl. The reaction was allowed to warm to room temperature and the organic layer was washed with saturated aq. NH4Cl, dried (MgSO4), filtered and evaporated and residue was purified by flash chromatography (20% ethyl acetate in hexane) to afford the sub-title compound as a pale yellow oil (3.437 g, 53%): 1H NMR (400 MHz CDCl3) δ 1.49 (9H, s), 1.60 (3H, d), 5.18 (1H, m), 7.27 (2H, m), 7.40 (1H, d), 7.59 (1H, t), 8.60 (1H, s).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at −78° C. for 1 h
  2. custombefore being quenched with saturated aq. NH4Cl
  3. washthe organic layer was washed with saturated aq. NH4Cl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customresidue was purified by flash chromatography (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-85117f94fa5c49a0aea414b6c41a10d3
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906650B2

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