Sodium Sulfite → HCID 29947824, compound

35% 11202 (0.240 mL, 2.91 mmol) was added to a solution of LiOH—H2O (0.0978 g, 2.33 mmol) in 2:1 THF:H2O (33 mL). The reaction mixture was stirred at room temperature for 35 minutes, and then cooled to 0° C. A solution containing a mixture of tert-butyl (S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-chlorophenyl)-3-oxopropylcarbamate (0.535 g, 1.17 mmol) and 2,4-dimethoxybenzaldehyde (0.194 g, 1.17 mmol) in THF (7 mL) was added dropwise by addition funnel. The ice bath was allowed to slowly warm, and the reaction mixture was stirred overnight. The reaction mixture was then cooled to 0° C., and 1M Na2SO3 (7 mL) was added. The mixture was stirred for 5 minutes, and then warmed to room temperature and stirred an additional 20 minutes. The reaction mixture was then transferred to a separatory funnel and washed with ether (3×). The aqueous layer was acidified with KHSO4(s), and the mixture was extracted with DCM (2×). The combined extracts were dried (Na2SO4), filtered, and concentrated to give (S)-3-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)propanoic acid (0.329 g, 94.2% yield) as a white residue. LC/MS (APCI+) m/z 200 [M-BOC+H]+.

1. temperaturecooled to 0° C
2. additionA solution containing
3. additionwas added dropwise by addition funnel
4. temperatureto slowly warm
5. stirringthe reaction mixture was stirred overnight
6. temperatureThe reaction mixture was then cooled to 0° C.
7. stirringThe mixture was stirred for 5 minutes
8. temperaturewarmed to room temperature
9. stirringstirred an additional 20 minutes
10. customThe reaction mixture was then transferred to a separatory funnel
11. washwashed with ether (3×)
12. extractionthe mixture was extracted with DCM (2×)
13. dry with materialThe combined extracts were dried (Na2SO4)
14. filtrationfiltered
15. concentrationconcentrated

ORD record

ord-2c1fbe8cf2604f3fac8540547957be71

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346789B2