2-Bromoethanol → [4-(2-Hydroxyethoxy)-2-methoxybenzyl]carbamic acid tert-butyl ester

HRID 2353602노트

반응식

HRID 2353602 반응식
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2].Br[CH2:20][CH2:21][OH:22]>CC(O)C.[OH-].[Na+]>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:20][CH2:21][OH:22])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 108982-BromoethanolHCID 68450274(4-Hydroxy-2-methoxybenzyl)carbamic acid tert-butyl ester

생성물 1

HCID 68452888[4-(2-Hydroxyethoxy)-2-methoxybenzyl]carbamic acid tert-butyl ester수율 38.5%

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
85 °C

실험 절차

To a stirred solution of (4-hydroxy-2-methoxy-benzyl)-carbamic acid tert-butyl ester (22.8 mg, 0.09 mmol) in 2-propanol (1 mL) and 2 N aq. NaOH (0.15 mL) is added 2-bromoethanol (22.5 mg, 0.18 mmol). The reaction mixture is heated to 85° C. and stirred for 8 h. The mixture is cooled to rt and subjected to prep. HPLC purification to give [4-(2-hydroxy-ethoxy)-2-methoxy-benzyl]-carbamic acid tert-butyl ester (10.3 mg) as a colourless oil. LC-MS: tR=0.85 min, [M+1]+=298.07.

후처리

  1. temperatureThe mixture is cooled to rt
  2. customHPLC purification

출처 및 근거

ORD 기록
ord-537e4b15fac44273bfa34e41ed9d749c
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750040B2

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