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

HRID 55558Notes

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-be541d90fafe46f8b47c768145e1a350
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05625075

Reaction notes

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