(R)-[4-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-phenyl]-tert-butoxycarbonylamino-acetic acid → (R)-tert-butoxycarbonylamino-[4-(2-hydroxy-1-hydroxymethyl-ethoxy)-phenyl]-acetic acid
Reaktionsgleichung
C([O:8][CH2:9][CH:10]([CH2:30][O:31]CC1C=CC=CC=1)[O:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1)C1C=CC=CC=1>CO>[C:26]([O:25][C:23]([NH:22][C@H:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH:10]([CH2:9][OH:8])[CH2:30][OH:31])=[CH:13][CH:14]=1)[C:19]([OH:21])=[O:20])=[O:24])([CH3:29])([CH3:28])[CH3:27]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A hydrogenation vessel containing a solution of (R)-[4-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-phenyl]-tert-butoxycarbonylamino-acetic acid (3.86 g, 7.4 mmol) in methanol (30 mL) was purged with nitrogen and 10% palladium on carbon (300 mg) added. The atmosphere above the methanol solution was exchanged for hydrogen and the reaction mixture stirred vigorously for 30 minutes at ambient temperature. The reaction mixture was filtered through a pad of celite and concentrated in vacuo to give (R)-tert-butoxycarbonylamino-[4-(2-hydroxy-1-hydroxymethyl-ethoxy)-phenyl]-acetic acid which was used without additional purification (2.43 g, 96%). HR-MS: calcd for C30H28FlN4O5 [M+H+] 671.1161. Found 671.1158.