Water → 3-[7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl]-5-isopropylidene-1,3-oxazolidin-2,4-dione

HRID 1109714Notes

Reaction equation

HRID 1109714 reaction equation
[F:1][C:2]1[C:15]([NH:16][C:17]([O:19][CH:20]([C:24](OC)=[O:25])[C:21]([CH3:23])=[CH2:22])=[O:18])=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.O1C2C=CC=CC=2C=CN1.O>C1(C)C=CC=CC=1.C[O-].[Na+]>[F:1][C:2]1[C:15]([N:16]2[C:24](=[O:25])[C:20](=[C:21]([CH3:22])[CH3:23])[O:19][C:17]2=[O:18])=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 157466857-fluoro-6-(1-methoxycarbonyl-2-methyl-2-propenyloxycarbonylamino)-4-propargyl-2H-1,4-benzoxazin-3(4H)-oneHCID 17845026Benzoxazines

Product 1

HCID 146486673-[7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl]-5-isopropylidene-1,3-oxazolidin-2,4-dione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 10942334Sodium MethoxideSolvent

Procedure

To a solution of 7-fluoro-6-(1-methoxycarbonyl-2-methyl-2-propenyloxycarbonylamino)-4-propargyl-2H-1,4-benzoxazin-3(4H)-one (10 g) in toluene (100 g), sodium methoxide was added in an amount of 0.05 equivalent to one equivalent of the benzoxazine. The resulting mixture was refluxed for 3 hours, cooled to room temperature, combined with water and extracted with ethyl acetate. The organic layer was washed with water three times, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography using a mixture of hexane and ethyl acetate as the eluent to give Compound No. 9 (6.1 g). m.p., 194°-198° C.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water three times
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. additiona mixture of hexane and ethyl acetate as the eluent
  8. customto give Compound No
  9. customm.p., 194°-198° C.

Sources & evidence

ORD record
ord-8dcf8ac16eb9457a935d71b8f72f64b8
Source dataset
uspto-grants-1994_06
Patent number
US05322835

Reaction notes

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