Triethylamine → N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N',N''-bis(tert-butoxycarbonyl)-N-[2-(tritylamino)ethyl]guanidine

HRID 459652

반응식

HRID 459652 반응식
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.FC(F)(F)S(N=[C:45]([NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58])[NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])(=O)=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH2:8][N:9]([CH2:10][CH2:11][NH:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:45]([NH:46][C:47]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:53])=[N:54][C:55]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:61]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 36945701,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidineHCID 18442411N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N'-tritylethane-1,2-diamine

생성물 1

HCID 68519459N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N',N''-bis(tert-butoxycarbonyl)-N-[2-(tritylamino)ethyl]guanidine수율 25.2%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N′-tritylethane-1,2-diamine (7.50 g) and triethylamine (2.86 g) in chloroform (100 ml) was added di-tert-butyl ({[(trifluoromethyl)sulfonyl]imino}-methylene)biscarbamate (11.05 g). The mixture was stirred at room temperature for 4 days. The reaction mixture was washed successively with 10% aqueous citric acid solution and brine, and the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 3% methanol/chloroform to give N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N′,N″-bis(tert-butoxycarbonyl)-N-[2-(tritylamino)ethyl]guanidine (3.00 g) as a solid.

후처리

  1. washThe reaction mixture was washed successively with 10% aqueous citric acid solution and brine
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with 3% methanol/chloroform

출처 및 근거

ORD 기록
ord-25b47db223204645b643fcf71cdc9cd0
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192943B2

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