Sodium Bicarbonate → Benzyl phenylcarbamate

HRID 2299656Notes

Reaction equation

HRID 2299656 reaction equation
C(NC1CCCC2C=CC(OC)=CC=2C1)C1C=CC=CC=1.[C:22]1([N:28](CC2OC2)[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>ClCCl.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[CH2:32]([O:31][C:29]([NH:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 18007303HCID 18007303, compoundHCID 180073081-(N-benzyloxycarbonyl-N-phenylamino)-2,3-epoxypropane

Product 1

HCID 319368Benzyl phenylcarbamateYield 127.6%

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, to a solution of N-benzyl-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (300 mg) and 1-[N-phenyl-N-benzyloxycarbonylamino]-2,3-epoxypropane (300 mg) in dichloromethane (5 ml) was added ytterbium(III) trifluoromethanesulfonate (66 mg) at room temperature, and the mixture was stirred at the same temperature for 24 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 to 4:1) to give N-[3-[N′-benzyl-N-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-2-hydroxypropyl[-N-benzyloxycarbonylphenylamine (307 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 to 4:1)

Sources & evidence

ORD record
ord-c372600311104b97affdc5d99d7bdb5a
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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