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

HRID 704539Notes

Reaction equation

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]

Participants

Reactant 3

HCID 4148881Lithium borohydride

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

HCID 6994036Z-Glu-OtBu

Product 1

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

Procedure

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.

Sources & evidence

ORD record: ord-6fd5b1239ca04a35b76e2134e474c8c9
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988496

Reaction notes

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