Sodium hydride → (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate

HRID 622370ノート

反応式

HRID 622370 の反応式
[CH:1]([C@H:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[C:14]([CH:15]([CH3:17])[CH3:16])[C:6]=2[O:5]1)([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>CN(C)C=O.O>[CH:1]([C@H:4]1[C:9](=[O:10])[N:8]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:7]2[CH:11]=[CH:12][CH:13]=[C:14]([CH:15]([CH3:17])[CH3:16])[C:6]=2[O:5]1)([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 7210282(S)-2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-one

生成物 1

HCID 14234720(S)-methyl 3,4-dihydro-2,8-diisopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate収率 81.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of (S)-2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-one (4.66 g) in dimethylformamide (60 ml), was added portionwise 60% sodium hydride in oil (0.84 g). The mixture was stirred at room temperature for 10 minutes, and a solution of methyl bromoacetate (2.0 ml) in dimethylformamide (6.0 ml) was added thereto. The whole was stirred at room temperature for 30 minutes, diluted with water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was crystallized from hexane to yield (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate as crystals (4.95 g, 81.1%). Recrystallization from hexane gave colorless needles, mp 67°-68° C. [α]D23 +3.7° (c=0.95, MeOH).

後処理

  1. stirringThe whole was stirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was crystallized from hexane

出典と根拠

ORDレコード
ord-9eabbaab1b31466eb8745f192c8983cf
出典データセット
uspto-grants-1988_09
特許番号
US04771050

反応ノート

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