(1S,2S)-[3-Chloro-1-(3,5-difluoro-benzyl)-2-hydroxy-propyl]-carbamic acid tert-butyl ester → (2S,3S)-3-amino-1-chloro-4-(3,5-difluorophenyl)butan-2-ol

tert-butyl (1S,2S)-3-chloro-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate (IV, EXAMPLE 3, 1.0 gm, 2.98 mmol) and Dowex50WX2-400 resin (4.6 gm, 23.8 mmol) and methanol (25 mL) are mixed. The mixture is then placed over a J-Kim shaker with heating at 50° for 2 hr. ESMS analysis indicates no starting material left in the mixture. The reaction contents are filtered through a sintered funnel and the resin washed with methanol (25 mL) and methanol/methylene chloride (1/1, 25 mL). The resulting mixture is eluted with ammonia in methanol (2N, 2×25 mL) The eluate is concentrated under reduced pressure to give the title compound, ESMS=236.1.

1. temperaturewith heating at 50° for 2 hr
2. waitleft in the mixture
3. customThe reaction contents
4. filtrationare filtered through a sintered funnel
5. washthe resin washed with methanol (25 mL) and methanol/methylene chloride (1/1, 25 mL)
6. washThe resulting mixture is eluted with ammonia in methanol (2N, 2×25 mL) The eluate
7. concentrationis concentrated under reduced pressure

ORD record

ord-0da384a52c7341eaac912606419e941c

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07638646B2