Methyl (S)-2-benzyloxycarbonylamino-4,4-difluoro-5-phenylpentanoate → Methyl (S)-2-amino-4,4-difluoro-5-phenylpentanoate

In a three-neck flask, methyl (S)-2-benzyloxycarbonylamino-4,4-difluoro-5-phenylpentanoate (1.0 g, 2.65 mmol) was dissolved in 25 ml of methanol. After repeated evacuation and sparging with argon, 350 mg of Pd/C (10%) were added. After degassing and sparging with argon again, the argon atmosphere was replaced by hydrogen (balloon with H2 gas). The mixture was stirred at RT for 3 h. Owing to incomplete conversion, a further 350 mg of catalyst were added and the mixture was hydrogenated at RT for a further 5 h. On completion of conversion, the reaction mixture was filtered. The mixture was washed with 20 ml of methanol and the filtrate was concentrated by evaporation under reduced pressure. A waxy residue was obtained which, as well as the desired product, also contained smaller amounts of the monodefluorinated and didefluorinated product. This residue was used without further purification for the further reaction.

1. customsparging with argon, 350 mg of Pd/C (10%)
2. additionwere added
3. customAfter degassing
4. customsparging with argon again
5. additionOwing to incomplete conversion, a further 350 mg of catalyst were added
6. waitthe mixture was hydrogenated at RT for a further 5 h
7. filtrationOn completion of conversion, the reaction mixture was filtered
8. washThe mixture was washed with 20 ml of methanol
9. concentrationthe filtrate was concentrated by evaporation under reduced pressure
10. customA waxy residue was obtained which

ORD record

ord-b23f5f4343ce406890f4abd9da76e756

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08039480B2