Sodium Bicarbonate → HCID 131724713, compound

HRID 1760728Notes

Reaction equation

HRID 1760728 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:18]2[CH:9]1[C:10]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:11]1[C:16]([CH2:17]2)=[CH:15][CH:14]=[C:13]([O:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.F[C:49](F)(F)S([O-])(=O)=O.[C:56](=[O:59])(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:23]([O:22][C:20](=[O:21])[O:19][C:13]1[CH:14]=[CH:15][C:16]2[CH2:17][C@@H:18]([O:59][CH2:56][CH3:49])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:10]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:11]=2[CH:12]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2733225Ytterbium triflateHCID 15923077HCID 15923077, compound

Product 1

HCID 131724713HCID 131724713, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-tert-Butoxycarbonyloxy-7,7-diethyl-1a,2,7,7a-tetrahydro 1-aza-cyclopropa[b]naphthalene-1-carboxylic acid tert-butyl ester (346.0 mg; 0.83 mmol) placed under Nitrogen was dissolved using anhydrous chloroform (15.0 mL) followed by 0.5 equivalents of Ytterbium trifluoromethanesulfonate (257.0 mg; 0.42 mmol) were then added. The reaction mixture was allowed to stir at room temperature overnight. The next day, it was poured into an aqueous solution of sodium bicarbonate and extracted using dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and the solvent was removed by vacuo. The crude was purified by flash chromatography using; hexanes:ethyl acetate (9:1) then (8:2) as the eluent. The isolated product is a solid (275 mg, 71%).

Workup

  1. dissolutionwas dissolved
  2. additionwere then added
  3. extractionextracted
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed by vacuo
  7. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-44c1374ab3904bd4b214e8015473da4c
Source dataset
uspto-grants-2005_01
Patent number
US06844368B1

Reaction notes

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