Lithium borohydride → (S)-tert-Butyl 4-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate

HRID 1648507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1648507
N(C(OCC1C=CC=CC=1)=O)[C@H](C(O[C:11]([CH3:14])([CH3:13])[CH3:12])=O)CCC(=O)O.[Li+].[BH4-].[NH:27]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:28]([C:34]([O:36]C(C)(C)C)=O)[CH2:29][CH2:30][C:31](=[O:33])[OH:32]>>[C:11]([O:32][C:31](=[O:33])[CH2:30][CH2:29][CH:28]([CH2:34][OH:36])[NH:27][C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])([CH3:14])([CH3:13])[CH3:12]

Komponenten

4

Edukt 3

HCID 4148881Lithium borohydrideHCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 6994036Z-Glu-OtBu

Produkt 1

HCID 4055117(S)-tert-Butyl 4-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate

Versuchsvorschrift

Cbz-Glu-OtBu 51 is converted to 52 via the methyl ester followed by LiBH4 reduction according to the procedure of Y. Hamada, M. Shibata, T. Sugiura, S. Kato and T. Shioiri, J. Org. Chem. 52:1242, 1987 used for the conversion of t-Boc-Glu-OtBu to the corresponding alcohol.

Quellen und Nachweise

ORD-Eintrag
ord-7188ae6e6c544ddda8b50fd5d7b937bf
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05436352

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