Water → 7-fluoro-6-(1-methoxycarbonyl-2-methyl-2-propenyloxycarbonylamino)-4-propargyl-2H-1,4-benzoxazin-3(4H)-one

HRID 1109718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109718
[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][CH3:24])=[O:22].C(N(CC)CC)C.O>C1C=CC=CC=1>[F:1][C:2]1[C:15]([NH:16][C:17]([O:19][CH:20]([C:21]([O:23][CH3:24])=[O:22])[C:25]([CH3:27])=[CH2:26])=[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

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 118174397-fluoro-6-isocyanato-4-propargyl-2H-1,4-benzoxazin-3(4H)-oneHCID 13461762Methyl 2-hydroxy-3-methylbut-3-enoate

Produkt 1

HCID 157466857-fluoro-6-(1-methoxycarbonyl-2-methyl-2-propenyloxycarbonylamino)-4-propargyl-2H-1,4-benzoxazin-3(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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), triethylamine (0.5 g) was added at room temperature. The resulting mixture was refluxed for 1 hour, 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. 72 (2.9 g). nD25.0 1.4868

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 1 hour
  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

Quellen und Nachweise

ORD-Eintrag
ord-f8c194ca2bef4632955007ab3fb3e406
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05322835

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