Water → 2-Benzyloxy-6-(4-tert-butoxycarbonylaminobutoxy)-benzoic Acid Methyl Ester

HRID 889275

반응식

HRID 889275 반응식
[CH3:1][O:2][C:3](=[O:24])[C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:24])[C:4]1[C:5]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10980693Methyl 2-{4-[(tert-butoxycarbonyl)amino]butoxy}-6-hydroxybenzoate

생성물 1

HCID 684315912-Benzyloxy-6-(4-tert-butoxycarbonylaminobutoxy)-benzoic Acid Methyl Ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(4-tert-butoxycarbonylamino-butoxy)-6-hydroxy-benzoic acid methyl ester (1.5 g, 4.4 mmol) in 20 mL of DMF is added benzyl bromide (0.56 mL, 4.6 mmol) and K2CO3 (1.8 g, 13.0 mmol) and the suspension is stirred at RT for 3 h. The mixture is poured into water and extracted with EtOAc. The organic layer is dried, filtered, and the solvent is removed under reduced pressure to give an oil that is purified by flash chromatography using a gradient of hexane/EtOAc (5:1 to 1:1) to give the product as a colorless liquid.

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. customthe solvent is removed under reduced pressure
  5. customto give an oil that
  6. customis purified by flash chromatography

출처 및 근거

ORD 기록
ord-92499a21116742afae35fc075768c6cb
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252820B2

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