Hydrochloric Acid → Tert-butyl N-tert-butoxycarbonyl-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)carbamate

HRID 1771652Notes

Reaction equation

HRID 1771652 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([F:22])=[CH:20][CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[C:17]=1[CH3:32])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:33].[Na+].OO.Cl>C1COCC1>[C:11]([O:10][C:9]([N:8]([C:16]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]([OH:33])[C:17]=1[CH3:32])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:15])([CH3:13])([CH3:14])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 89445558[3-(Di-Boc-amino)-4-fluoro-2-methylphenyl]boronic Acid Pinacol Ester

Product 1

HCID 89444253Tert-butyl N-tert-butoxycarbonyl-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)carbamateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-tert-butoxycarbonyl-N-[6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (800 mg, 41.7 mmol, 1.0 eq) in a mixture of THF (10 mL) and NaOH (1M aqueous solution, 5.3 mL, 5.3 mmol, 3.0 eq) at 0° C. was added H2O2 (30% aqueous solution, 603 mg, 5.32 mmol, 3.0 eq). The reaction mixture was stirred at room temperature for 3 h. The resulting mixture was acidified to pH 5-7 by addition of diluted HCl, and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography, (EtOAc:petroleum ether, 0:1 to 1:10) to give the title product as an oil (500 mg, 83%).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by column chromatography, (EtOAc:petroleum ether, 0:1 to 1:10)

Sources & evidence

ORD record
ord-36acdb841fd448c694550e3dd301313b
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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