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

反応式

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]

参加物

反応物 3

HCID 4148881Lithium borohydride

HCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid

HCID 6994036Z-Glu-OtBu

生成物 1

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

実験手順

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.

出典と根拠

ORDレコード: ord-676b5c03cf8344c3bcce50d3fa8a5cf6
出典データセット: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05075099

反応ノート

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