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

HRID 1645310ノート

反応式

HRID 1645310 の反応式
[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.[Pt]>[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

参加物

7

反応物 4

HCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate2 回HCID 21226206Ethyl acetate hexaneHCID 220309121-(Benzyloxy)-2-fluoro-4-nitrobenzene

生成物 1

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

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 34.9 g of 1-benzyloxy-2-fluoro-4-nitrobenzene (WO 03 064413) (MW: 247.28, 141 mmol) and 340 mg of platinum (5% on activated carbon) in 350 ml of ethyl acetate was stirred at RT and normal pressure under a hydrogen atmosphere. The course of the reaction was monitored by HPLC and the reaction was terminated after 20 h. The catalyst was filtered off and the filtrate was concentrated to dryness under reduced pressure using a rotary evaporator. The oily residue was dissolved in 500 ml of acetone and 250 ml of a saturated sodium hydrogen carbonate solution and 17.5 g of sodium hydrogen carbonate (MW: 84.01, 208 mmol) were added. The mixture was cooled to 5° C. and 26.08 g of benzyl chloroformate (MW: 170.59, 152 mmol) were added dropwise. The mixture was then stirred for 2 h at RT and the course of the reaction was monitored by TLC (hexane/ethyl acetate 3:1). The acetone was removed under reduced pressure, 500 ml of water were added to the residue, and the solid material was filtered off. The crystals were washed with 500 ml of water and dried.

後処理

  1. customthe reaction was terminated after 20 h
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure
  4. customa rotary evaporator
  5. dissolutionThe oily residue was dissolved in 500 ml of acetone
  6. temperatureThe mixture was cooled to 5° C.
  7. stirringThe mixture was then stirred for 2 h at RT
  8. customThe acetone was removed under reduced pressure, 500 ml of water
  9. additionwere added to the residue
  10. filtrationthe solid material was filtered off
  11. washThe crystals were washed with 500 ml of water
  12. customdried

出典と根拠

ORDレコード
ord-fd5998b5f87a4609921e891df7662174
出典データセット
uspto-grants-2012_02
特許番号
US08124772B2

反応ノート

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