Ammonium Chloride → HCID 53882279, compound

HRID 377576Notes

Reaction equation

HRID 377576 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[CH2:11][C:12]1[O:17][CH2:16][N:15]([C:18]([CH3:27])([CH3:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14](=[O:28])[C:13]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Cl-].[NH4+]>ClCCl>[F:7][CH2:11][C:12]1[O:17][CH2:16][N:15]([C:18]([CH3:27])([CH3:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14](=[O:28])[C:13]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 123472(Diethylamino)sulfur trifluorideHCID 57067707HCID 57067707, compound

Product 1

HCID 53882279HCID 53882279, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulphur trifluoride (1.27 ml) was added to a stirred solution of tert butyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (3.5 g) in dichloromethane at -78° C. After 0.5 hour the solution was allowed to warm to room temperature and stirred for 16 hours. The mixture was poured into saturated ammonium chloride solution and the organic phase washed (brine), dried (magnesium sulphate) and evaporated. The residue was purified by dry column chromatography on silica get, eluting with dichloromethane/hexane (1:1) to give tert butyl 2-(6-fluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (1.31 g) as a white solid, m.p. 80.5-82.5° C.

Workup

  1. washthe organic phase washed (brine)
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated
  4. customThe residue was purified
  5. customby dry column chromatography on silica
  6. customget
  7. washeluting with dichloromethane/hexane (1:1)

Sources & evidence

ORD record
ord-d49249b13e7848829586576f18afc52d
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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