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Diisopropylethylamine → N,N'-bis(tert-butoxycarbonyl)-N''-(1-(4-methylpyridin-2-yl)pyrrolidin-3-yl)guanidine

HRID 1059895
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반응식

HRID 1059895 반응식
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=2)[CH2:3]1.[C:14]([O:18][C:19]([NH:21][C:22]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=S)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C.[I-].C[N+]1C=CC=CC=1Cl>ClCCl.C(OCC)(=O)C>[C:28]([O:27][C:25]([NH:24][C:22]([NH:21][C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])=[N:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=2)[CH2:3]1)=[O:26])([CH3:31])([CH3:30])[CH3:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 5193990N,N'-Di-Boc-thioureaHCID 186675373-Amino-1-(4-methylpyridin-2-yl)pyrrolidine

생성물 1

HCID 18667639N,N'-bis(tert-butoxycarbonyl)-N''-(1-(4-methylpyridin-2-yl)pyrrolidin-3-yl)guanidine수율 69.2%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 3-amino-1-(4-methylpyridin-2-yl)pyrrolidine (177 mg) and N,N′-bis(tert-butoxycarbonyl)thiourea (331 mg) and diisopropylethylamine (0.4 ml) in dichloromethane (10 ml) was added 1-methyl-2-chloropyridinium iodide (332 mg), and the mixture was stirred for 16 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, n-hexane:ethyl acetate=4:1) and crystallized from diisopropyl ether to give N,N′-bis(tert-butoxycarbonyl)-N″-(1-(4-methylpyridin-2-yl)pyrrolidin-3-yl)guanidine (290 mg).

후처리

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 25 g, n-hexane:ethyl acetate=4:1)
  5. customcrystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-5d757d61752840fa84bf33554e578726
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06521643B1

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