Triethylamine → 2-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamate

HRID 459617

反応式

HRID 459617 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(O)(O)(=O)=O.[CH3:30][N:31]1[C:35]([NH2:36])=[C:34]([NH2:37])[CH:33]=[N:32]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>O>[NH2:36][C:35]1[N:31]([CH3:30])[N:32]=[CH:33][C:34]=1[NH:37][C:13](=[O:15])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:16][NH:17][C:18](=[O:19])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2756240L-N-Cbz-3-N-Boc-Amino-alanineHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

生成物 1

HCID 865978712-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamate収率 82.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a suspension of (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoic acid (1.695 g) and 1-methyl-1H-pyrazole-4,5-diamine sulfate (1.05 g) in water (16 ml) were added triethylamine (1.4 ml) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.73 g). The mixture was stirred at room temperature for 2 hours. The resulting suspension was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 2-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamate (1.78 g) as a solid.

後処理

  1. extractionThe resulting suspension was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a741ffa55af24e959b6013c00659832b
出典データセット
uspto-grants-2007_03
特許番号
US07192943B2

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