Methanol → 3-Benzyloxycarbonylamino-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C:9](=O)[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C[OH:38]>>[C:1]([O:5][C:6](=[O:34])[CH:7]([OH:38])[CH:8]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:9][CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Edukt 3

HCID 887Methanol

HCID 4311764Sodium borohydride

HCID 865944013-Benzyloxycarbonylamino-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

Produkt 1

HCID 866130753-Benzyloxycarbonylamino-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl esterAusbeute 81 %

Versuchsvorschrift

To a dry round bottom flask equipped with a magnetic stir bar was added composition 12 (189 mg, 0.38 mM, 1 equiv) and MeOH (20 mL). With constant stirring was added NaBH4 (8 mg, 0.228 mmol, 0.6 equiv). Upon addition gas bubbles were produced and the resulting clear colorless solution was stirred at 0° C. for 30 minutes. Solvent was removed in vacuo and the resulting solid was purified via column chromatography (silica gel, 2:1, hexanes/EtOAc) to give 13 as a sticky white solid. (165 mg, 0.34 mmol, 81% yield) ESMS: 488.2 (M+H+), 510.8 (M+Na+).