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Ethylene Glycol → tert-butyl (3R)-4-[3-(2-hydroxyethoxy)pyrazin-2-yl]-3-methylpiperazine-1-carboxylate

HRID 1295727
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HRID 1295727 반응식
Cl[C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@H:9]2[CH3:21])=[N:4][CH:5]=[CH:6][N:7]=1.[CH2:22]([OH:25])[CH2:23][OH:24].CC([O-])(C)C.[K+]>CS(C)=O>[OH:24][CH2:23][CH2:22][O:25][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@H:9]2[CH3:21])=[N:4][CH:5]=[CH:6][N:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 23665647Potassium tert-butoxideHCID 86591091(R)-tert-butyl 4-(3-chloropyrazin-2-yl)-3-methylpiperazine-1-carboxylate

생성물 1

HCID 69366745tert-butyl (3R)-4-[3-(2-hydroxyethoxy)pyrazin-2-yl]-3-methylpiperazine-1-carboxylate수율 87%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
50 °C

실험 절차

A mixture of tert-butyl (3R)-4-(3-chloropyrazin-2-yl)-3-methylpiperazine-1-carboxylate* (35 g, 0.11 mol), ethylene glycol (100 g, 1.61 mol) and t-BuOK (25 g, 0.22 mol) in DMSO (150 g) was stirred at 50° C. for 3 h. After this time, the reaction mixture was partitioned between EtOAc (500 g) and water (500 g) and sodium chloride (20 g) was added. The organic layer was concentrated in vacuo to furnish 32.5 g (87%) of the title product. HPLC purity: 75%. HRMS m/z calcd for C16H26N4O4 (M)+ 338.1954, found 338.1959. *Described in WO 00/76984, Example 172, Step 2.

후처리

  1. customAfter this time, the reaction mixture was partitioned between EtOAc (500 g) and water (500 g) and sodium chloride (20 g)
  2. additionwas added
  3. concentrationThe organic layer was concentrated in vacuo

출처 및 근거

ORD 기록
ord-0e0738a5d6b84072a849fcf60a9332a9
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07244722B2

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