4-Aminophenol → tert-Butyl 3-amino-4-hydroxybenzoate

HRID 25263

반응식

HRID 25263 반응식
N[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([O:16]C(OC(C)(C)C)=O)=O)([CH3:12])([CH3:11])[CH3:10].C([N:27](C(C)C)CC)(C)C>C1COCC1>[C:14]([C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([NH2:27])[CH:3]=1)([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:16]

참가 물질

5

반응물 3

HCID 4034-AminophenolHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonate

생성물 1

HCID 11160103tert-Butyl 3-amino-4-hydroxybenzoate수율 96.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-aminophenol (10.9 g, 100 mmol) in THF (150 mL) cooled in an ice bath was added di-tert-butyl-dicarbonate (21.8 g, 100 mmol) followed by diisopropylethylamine (17.4 mL, 100 mmol). The mixture was stirred at room temperature overnight and concentrated. The residue was taken up in ethyl acetate and the solution was washed with brine, dried (MgSO4), and concentrated. Purification on a silica gel column eluting with 5% methanol/40% ethyl acetate hexane gave 4Boc-aminophenol (20.1 g, 96%). MS(NH3—CI): (M+NH3+H)=227.

후처리

  1. concentrationconcentrated
  2. washthe solution was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification on a silica gel column
  6. washeluting with 5% methanol/40% ethyl acetate hexane

출처 및 근거

ORD 기록
ord-a263a6c6aab24b52ae051db78b79b634
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858626B2

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