Reaktion #83836

ord-be541d90fafe46f8b47c768145e1a350

Reaktionsgleichung

CC(C)(C)OC(=O)N[C@@H](CCC(=O)O)C(=O)OC(C)(C)C
t-Boc-Glu-OtBu
CC(C)(C)OC(=O)[C@H](CCC(=O)O)NC(=O)OCc1ccccc1
Cbz-Glu-OtBu
[BH4-].[Li+]
LiBH4
→
CC(C)(C)OC(=O)CCC(CO)NC(=O)OC(C)(C)C
4-Hydroxymethyl-4-(t-butoxycarbonyl)aminobutanoic acid-t-butyl ester

Edukte

CC(C)(C)OC(=O)N[C@@H](CCC(=O)O)C(=O)OC(C)(C)C
t-Boc-Glu-OtBu
CC(C)(C)OC(=O)[C@H](CCC(=O)O)NC(=O)OCc1ccccc1
Cbz-Glu-OtBu
—
methyl ester
—
alcohol
[BH4-].[Li+]
LiBH4

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05625075uspto-grants-1997_04