Benzyl chloroformate → Benzyl [4-(benzyloxy)-3-fluorophenyl]carbamate

HRID 1888853노트

반응식

HRID 1888853 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].CCCCCC.C(OCC)(=O)C>C(OCC)(=O)C>[CH2:28]([O:27][C:25](=[O:26])[NH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([F:18])[CH:11]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

6

반응물 4

HCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate2회HCID 21226206Ethyl acetate hexaneHCID 220309121-(Benzyloxy)-2-fluoro-4-nitrobenzene

생성물 1

HCID 57754845Benzyl [4-(benzyloxy)-3-fluorophenyl]carbamate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A solution of 34.9 g 1-benzyloxy-2-fluoro-4-nitro-benzene (WO03064413) (MW: 247.28, 141 mmol) and 340 mg platinium 5% on activated carbon in 350 ml ethyl acetate was stirred under hydrogen at rt and normal pressure. The reaction was monitored by HPLC and was complete after twenty hours. The catalyst was filtered over a glass fiber filter, and the filtrate evaporated under reduced pressure to dryness. The oily residue was dissolved in 500 ml acetone and treated with 250 ml of a saturated solution of sodium bicarbonate and 17.5 g of sodium bicarbonate (MW: 84.01, 208 mmol). The mixture was cooled to 5° C. and treated drop wise with 26.08 g of benzyl chloroformate (MW: 170.59, 152 mmol). The reaction was allowed to stirred at room temperature for two hours and monitored by TLC (hexane/ethyl acetate 3:1). The acetone was evaporated, the residue diluted with 500 ml water, and the solid filtered off. The crystals were washed with 500 ml water and dried. Yield: 48.05 g, 95.8%. MS: 352.5 (M+H)+, 350.8, (M−H)−. Method ESI+, ESI−.

후처리

  1. waitwas complete after twenty hours
  2. filtrationThe catalyst was filtered over a glass fiber
  3. filtrationfilter
  4. customthe filtrate evaporated under reduced pressure to dryness
  5. dissolutionThe oily residue was dissolved in 500 ml acetone
  6. temperatureThe mixture was cooled to 5° C.
  7. stirringto stirred at room temperature for two hours
  8. customThe acetone was evaporated
  9. additionthe residue diluted with 500 ml water
  10. filtrationthe solid filtered off
  11. washThe crystals were washed with 500 ml water
  12. customdried

출처 및 근거

ORD 기록
ord-7057782b28794a7883e7d3f842337f25
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501774B2

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