Ammonium Chloride → HCID 10379906, compound

HRID 2217346Notes

Reaction equation

C([Li])CCC.[CH3:6][C@H:7]1[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:10][C:9](=[O:18])[NH:8]1.[Br:19][CH2:20][C:21](Cl)=[O:22].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>CCCCCC.O1CCCC1.O>[Br:19][CH2:20][C:21]([N:8]1[C@@H:7]([CH3:6])[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:10][C:9]1=[O:18])=[O:22]

Participants

Conditions

Temperature: -70 °C

Procedure

82 ml of a 2.5 molar solution of butyllithium in hexane is added to a solution of 33.06 g (186.6 mmol) of (4S,5R)-4-methyl-5-phenyloxazolidin-2-one in 500 ml of tetrahydrofuran within 30 minutes at −70° C. under argon. Then, a solution of 15.55 ml (187 mmol) of bromoacetyl chloride in 250 ml of tetrahydrofuran is added in drops in such a way that the internal temperature does not exceed −65° C. Then, it is stirred for one more hour at −70° C. Then, the reaction mixture is poured onto 50 ml of saturated aqueous ammonium chloride solution. 90 ml of saturated aqueous sodium bicarbonate solution is then added, allowed to come to 25° C., diluted with water and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, dried on sodium sulfate and chromatographed on silica gel. 42.32 g (76%) of the title compound is obtained.

Workup

customdoes not exceed −65° C
customto come to 25° C.
extractionextracted with ethyl acetate
washThe organic phase is washed with saturated aqueous sodium chloride solution
customdried on sodium sulfate
customchromatographed on silica gel

Sources & evidence

ORD record: ord-9f3625c59e6a474db7e735ac9c03f036
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407975B2

Reaction notes

Loading…