Acetic Acid → [2-(2-Benzyloxyphenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester

HRID 1694902Notes

Reaction equation

HRID 1694902 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([O:19][C:20](=[O:27])[NH:21][C:22]([CH3:26])([CH3:25])[CH:23]=O)([CH3:18])([CH3:17])[CH3:16].[CH2:28]([O:35][C:36]1[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=1[NH2:38])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:15]([O:19][C:20](=[O:27])[NH:21][C:22]([CH3:26])([CH3:25])[CH2:23][NH:38][C:37]1[CH:39]=[CH:40][CH:41]=[CH:42][C:36]=1[O:35][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 2405482-BenzyloxyanilineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

Product 1

HCID 66645956[2-(2-Benzyloxyphenylamino)-1,1-dimethylethyl]carbamic acid t-butyl esterYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.38 g of sodium triacetoxyborohydride (30.1 mmol) was added to a solution of 4.68 g of (1,1-dimethyl-2-oxoethyl)carbamic acid t-butyl ester obtained in Reference Example 3 (25.0 mmol), 5.0 g of 2-benzyloxyaniline (25.0 mmol) and 1.44 ml of acetic acid (25.0 mmol) in methylene chloride (250 ml) under ice-cooling, and the mixture was stirred at room temperature for 16 hours. A saturated sodium bicarbonate aqueous solution was added to the reaction mixture, followed by extraction with methylene chloride. Then, the organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=5/1) to obtain 8.50 g of the title compound (yield: 91%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with methylene chloride
  3. washThen, the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-50ba56b8b8574819a2106f66ca9228b4
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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