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

HRID 622370노트

반응식

HRID 622370 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9eabbaab1b31466eb8745f192c8983cf
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04771050

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