Sodium hydride → Methyl 2-((bis(tert-butoxycarbonyl)amino)methyl)-5-fluorobenzoate

HRID 2252807노트

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HRID 2252807 반응식
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:2]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].[H-].[Na+].Br[CH2:19][C:20]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]>CN(C=O)C>[C:12]([O:11][C:9]([N:1]([CH2:19][C:20]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])[C:2]([O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[O:3])=[O:10])([CH3:15])([CH3:14])[CH3:13]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 279800Di-tert-butyl IminodicarboxylateHCID 15155455Methyl 2-(bromomethyl)-5-fluorobenzoate

생성물 1

HCID 58978006Methyl 2-((bis(tert-butoxycarbonyl)amino)methyl)-5-fluorobenzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

In a dry flask under nitrogen, di-tert-butyl iminodicarboxylate (Aldrich, 3.86 g, 17.8 mmol) was dissolved in dry DMF (5 mL) and treated with NaH (60% dispersion in oil, 0.71 g, 17.8 mmol). After the evolution of gas had ceased, Methyl 2-(bromomethyl)-5-fluorobenzoate (4 g, 16.2 mmole) dissolved in DMF (5 mL) was added. An additional 5 mL of DMF was added to aid stirring. The reaction was stirred for 2 hrs, then partitioned between water and EtOAc. The organic layer was dried with Na2SO4, filtered and concentrated and the residue was purified on silica eluting first with toluene, then with a gradient of 0-5% MeOH(CHCl3. The impure product thus obtained was re-chromatographed on silica eluting with a gradient of 0-30% EtOAc/Hexanes. The product was obtained as a clear oil.

후처리

  1. additionwas added
  2. stirringThe reaction was stirred for 2 hrs
  3. custompartitioned between water and EtOAc
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified on silica eluting first with toluene
  8. customThe impure product thus obtained
  9. customwas re-chromatographed on silica eluting with a gradient of 0-30% EtOAc/Hexanes
  10. customThe product was obtained as a clear oil

출처 및 근거

ORD 기록
ord-54da8dd3562a4757b5d75d656b7142c3
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323460B2

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