Carbonic acid, bis(1,1-dimethylethyl) ester → HCID 86607644, compound

HRID 2114164Notes

Reaction equation

HRID 2114164 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([NH2:16])=[C:11]([Br:17])[C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24](=O)[O:25]C(C)(C)C)([CH3:22])([CH3:21])[CH3:20]>C1COCC1.CN(C)C1C=CN=CC=1>[C:19]([O:23][C:24](=[O:25])[NH:16][C:12]1[CH:13]=[C:14]([F:15])[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([F:18])[C:11]=1[Br:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 23130240HCID 23130240, compound

Product 1

HCID 86607644HCID 86607644, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyloxy-2-bromo-3,5-difluorophenylamine (3.33 g) in THF (35 mL) were added di-tert-butylcarbonate (6.95 g) and 4-dimethylaminopyridine (130 mg), and the mixture was heated under reflux for 2 hours. The reaction mixture was allowed to stand for cooling to room temperature, and concentrated. The residue was diluted with ethyl acetate and washed with 0.5N hydrochloric acid and saturated aqueous brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1) to give (4-benzyloxy-2-bromo-3,5-difluorophenyl)carbamic acid tert-butyl ester (3.9 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with 0.5N hydrochloric acid and saturated aqueous brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-3932d67713d44c7d888c95aef521a517
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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