Carbon Tetrachloride → HCID 9862135, compound

HRID 1108556Notes

Reaction equation

HRID 1108556 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:16]2[CH2:20][CH:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][N:17]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][C:10]([CH:13]=[N:14]O)=[CH:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(#N)C>[C:13]([C:10]1[CH:11]=[CH:12][N:8]([C:7]2[CH:6]=[CH:5][C:4]([C:16]3[CH2:20][CH:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][N:17]=3)=[CH:3][C:2]=2[F:1])[CH:9]=1)#[N:14]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 54463452HCID 54463452, compound

Product 1

HCID 9862135HCID 9862135, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(-)-5-Acetamidomethyl-3-(3-fluoro-4-(3-hydroximino-pyrrol-1-yl)phenyl)isoxazoline (Example 16) (486 mg) is combined with triphenylphosphine (1.48 g) and carbon tetrachloride (0.816 ml) in 14 ml acetonitrile in a 50 ml one neck round bottom flask under nitrogen. The mixture is stirred 1 hour at room temperature and the volatiles are removed in vacuo to give a pale yellow oil. The crude material is chromatographed over 35 g silica gel (230-400 mesh) eluting with 4% methanol/dichloromethane while collecting 5 ml fractions. Fractions 39-50 are combined and concentrated to give 224 mg of a white solid. The solid is washed with diethyl ether and is dried to give 160 mg of the title compound as a white solid, mp 159-161° C., [α]25D -72° (c 0.53, DMSO).

Workup

  1. customthe volatiles are removed in vacuo
  2. customto give a pale yellow oil
  3. customThe crude material is chromatographed over 35 g silica gel (230-400 mesh)
  4. washeluting with 4% methanol/dichloromethane
  5. customwhile collecting 5 ml fractions
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e34f5c3c818a44a5b1867f3e375c7e35
Source dataset
uspto-grants-2000_05
Patent number
US06069141

Reaction notes

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