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

HRID 459652

反応式

HRID 459652 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-25b47db223204645b643fcf71cdc9cd0
出典データセット
uspto-grants-2007_03
特許番号
US07192943B2

関連ノート

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