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

HRID 55558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 55558
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-be541d90fafe46f8b47c768145e1a350
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05625075

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