Acetic Acid → 5-[(R)-2-amino-1-(tert-butyldimethylsilyloxy)ethyl]-2-hydroxyphenylformamide acetate
Reaction equation
C([NH:8][CH2:9][C@@H:10]([C:19]1[CH:20]=[CH:21][C:22]([O:28]CC2C=CC=CC=2)=[C:23]([NH:25][CH:26]=[O:27])[CH:24]=1)[O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])C1C=CC=CC=1.[C:36]([OH:39])(=[O:38])[CH3:37]>CO>[C:36]([OH:39])(=[O:38])[CH3:37].[NH2:8][CH2:9][C@@H:10]([C:19]1[CH:20]=[CH:21][C:22]([OH:28])=[C:23]([NH:25][CH:26]=[O:27])[CH:24]=1)[O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Crude N-{5-[(R)-2-benzylamino-1-(tert-butyldimethylsilanyloxy)ethyl]-2-benzyloxyphenyl}formamide (100 g, 194 mmol) was dissolved in methanol (1 L) and acetic acid (25 mL, 291 mmol). The resulting mixture was purged with dry nitrogen and then palladium hydroxide on carbon (20 g, 20 wt. %, about 50% water) was added. Hydrogen was bubbled through the reaction mixture with stirring at room temperature for about 10 hours. The mixture was then purged with dry nitrogen and the mixture was filtered through Celite. The filtrate was concentrated on a rotary evaporator and ethyl acetate (600 mL) was added to the residue. This mixture was stirred for about 2 hours at which time a thick yellow slurry had developed. The slurry was filtered and the precipitate was air dried to provide N-{5-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-2-hydroxyphenyl}formamide acetic acid salt (48 g, 98% purity) as a yellow-white solid. LCMS (10-70) Rt=3.62; [M+H+] found 311.3.