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

HRID 1109718ノート

反応式

HRID 1109718 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-f8c194ca2bef4632955007ab3fb3e406
出典データセット
uspto-grants-1994_06
特許番号
US05322835

反応ノート

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