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Potassium Carbonate → 3-(4-tert-Butoxycarbonylmethoxy-3-chloro-phenyl)-propionic acid benzyl ester

HRID 2170113
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HRID 2170113 반응식
[CH2:1]([O:8][C:9](=[O:20])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([Cl:19])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C=O)C.O>[CH2:1]([O:8][C:9](=[O:20])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[C:14]([Cl:19])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 667975723-(3-Chloro-4-hydroxy-phenyl)-propionic acid benzyl ester

생성물 1

HCID 667975133-(4-tert-Butoxycarbonylmethoxy-3-chloro-phenyl)-propionic acid benzyl ester

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

3-(3-Chloro-4-hydroxy-phenyl)-propionic acid benzyl ester (step 1) (5.9 g, 20.3 mmol) in DMF (60 ml) was treated with potassium carbonate (5.61 g, 40.6 mmol) followed by t-butyl bromoacetate (4.49 ml, 30.4 mmol) and the mixture was heated at 60° C. overnight. The reaction mixture was diluted with water (500 ml), and the product extracted into EtOAc (450 ml). The organic portion was washed with water (200 ml), brine (200 ml), dried over MgSO4 and the solvent removed in vacuo to yield a yellow oil. Purification by chromatography on silica eluting with 0-20% EtOAc in iso-hexane afforded the title product; 1H NMR (400 MHz, DMSO-d6) δ 7.34 (6H, m), 7.11 (1H, d), 6.89 (1H, d), 5.07 (2H, s), 4.74 (2H, s), 2.81 (2H, t), 2.68 (2H, t), 1.42 (9H,s). LC-MS Rt 1.64 mins; 427.3 [M+Na]+, Method 2minLC_v002.

후처리

  1. extractionthe product extracted into EtOAc (450 ml)
  2. washThe organic portion was washed with water (200 ml), brine (200 ml)
  3. dry with materialdried over MgSO4
  4. customthe solvent removed in vacuo
  5. customto yield a yellow oil
  6. customPurification by chromatography on silica eluting with 0-20% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-39243c9441b2484e8fc39bfdd5718be0
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09050339B2

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