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

HRID 1109719Notes

Reaction equation

HRID 1109719 reaction equation
[F:1][C:2]1[C:15]([N:16]=[C:17]=[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.[OH:19][CH:20]([C:25]([CH3:27])=[CH2:26])[C:21]([O:23]C)=O.C1CCN2C(=NCCC2)CC1.O>C1C=CC=CC=1>[F:1][C:2]1[C:15]([N:16]2[C:21](=[O:23])[C:20](=[C:25]([CH3:27])[CH3:26])[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 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 118174397-fluoro-6-isocyanato-4-propargyl-2H-1,4-benzoxazin-3(4H)-oneHCID 13461762Methyl 2-hydroxy-3-methylbut-3-enoate

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 1

HCID 241BenzeneSolvent

Procedure

To a solution of 7-fluoro-6-isocyanato-4-propargyl-2H-1,4-benzoxazin-3(4H)-one (2.5 g) and methyl 2-hydroxy-3-methyl-3-butenoate (1.3 g) in benzene (50 ml), DBU (1.5 g) was added at room temperature. The resulting mixture was refluxed for 10 hours, cooled to room temperature, combined with water and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography using a mixture of toluene and ethyl acetate as the eluent to give Compound No. 9 (3.0 g).

Workup

  1. temperatureThe resulting mixture was refluxed for 10 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. additiona mixture of toluene and ethyl acetate as the eluent
  8. customto give Compound No

Sources & evidence

ORD record
ord-739631156dfb4d019882bfd3964d98a5
Source dataset
uspto-grants-1994_06
Patent number
US05322835

Reaction notes

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