Tetrahydrofuran → HCID 12638305, 화합물

HRID 1903363노트

반응식

HRID 1903363 반응식
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:3]1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1.C1COCC1.[H-].[Na+].Br[CH2:38][C:39]([O:41][CH3:42])=[O:40]>O>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][N:7]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:2](=[O:1])[CH:3]1[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:21]=1)=[O:9])([CH3:13])([CH3:14])[CH3:12]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 12638302HCID 12638302, 화합물

생성물 1

HCID 12638305HCID 12638305, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of t-boc-(4-benzyloxybenzyl) piperazinone 3a (2.66 g, 6.72 ×10-3 mole) and dry THF (20 ml) under argon at room temperature is added portionwise NaH (0.30 g, 7.4 ×10-3 mole, 59% oil dispersion). After stirring 1/2hour at room temperature a solution of methyl α-bromoacetate (0.62 ml, 7.4 ×10-3 mole) is added via syringe. After stirring overnight the reaction mixture is poured into water which is subsequently extracted with Et2O (3 times). The combined ethereal extracts are washed with saturated aqueous NaCl before being dried over Na2SO4. Filtration of the drying agent and evaporation of the filtrate affords a viscous oil which after column chromatography (silica gel, 10% EtOAc/CHCl3)gives a clear, colorless oil. After standing in the refrigerator this oil crystallizes. The resulting solid is triturated with hexane and collected by filtration affording 4a as colorless matted needles: 2.3 g (74%), m.p. 84°-87° C.

후처리

  1. additionis added via syringe
  2. extractionis subsequently extracted with Et2O (3 times)
  3. washThe combined ethereal extracts are washed with saturated aqueous NaCl
  4. dry with materialbefore being dried over Na2SO4
  5. filtrationFiltration of the drying agent and evaporation of the filtrate
  6. customaffords a viscous oil which after column chromatography (silica gel, 10% EtOAc/CHCl3)
  7. customgives a clear, colorless oil
  8. customcrystallizes
  9. customThe resulting solid is triturated with hexane
  10. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-28b67659267d4ac6ac38e8ef0c351e18
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04435571

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