Ethyl bromoacetate → (4-tert-Butoxycarbonylamino-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

HRID 1726961노트

반응식

HRID 1726961 반응식
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([OH:18])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CC(C)=O>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][O:18][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:19])=[CH:9][CH:10]=1)[CH3:32]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamate

생성물 1

HCID 69037445(4-tert-Butoxycarbonylamino-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

3.33 g (12.8 mmol) of 4-hydroxy-naphthalen-1-yl-carbamic acid tert-butyl ester was dissolved in 60 ml of acetone and treated at 0° C. subsequently with 4.60 g (1.1 eq.) of cesium carbonate, 0.107 g (0.05 eq.) of KI, and 1.42 ml (1.0 eq.) of ethyl bromoacetate. After vigorous stirring for 1 h at ambient temperature, the solvent was evaporated and the residue redissolved in AcOEt. Washing with water, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=75/25), yielded 4.28 g of the title product as off-white crystals.

후처리

  1. customthe solvent was evaporated
  2. dissolutionthe residue redissolved in AcOEt
  3. washWashing with water
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

출처 및 근거

ORD 기록
ord-403b5e2d0f9c4a02984296bbf404cf8e
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495001B2

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