Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 131724713, compound

HRID 1760727Notes

Reaction equation

HRID 1760727 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].[C:31]1([CH3:41])C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-:49].[Na+]>C(O)C>[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:49][CH2:31][CH3:41])[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 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 15923077HCID 15923077, compound

Product 1

HCID 131724713HCID 131724713, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-tert-Butoxycarbonyloxy-7,7-diethyl-1a,2,7,7a-tetrahydro-1-aza-cyclopropa[b]naphthalene-1-carboxylic acid tert-butyl ester (224.0 mg, 0.54 mmol) placed under Argon at room temperature was dissolved in anhydrous ethanol (8.0 mL). To this solution was added a catalytic amount of pyridinium p-toluene sulfonate. The reaction mixture was stirred overnight. The next day, the reaction mixture was poured into an aqueous solution of sodium bicarbonate and it was extracted using dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and the solvent was removed. 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 (129 mg, 55%).

Workup

  1. customplaced under Argon at room temperature
  2. extractionwas extracted
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed
  6. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-5e48f6f679b0488f8106535d7b2de410
Source dataset
uspto-grants-2005_01
Patent number
US06844368B1

Reaction notes

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