Water → HCID 178481900, 화합물

HRID 459618

반응식

HRID 459618 반응식
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:31])[C@@H:10](NC(=O)OCC1C=CC=CC=1)[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C.FC(F)(F)S([N:44]=[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.O>O1CCCC1.[Pd]>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:31])[C@@H:10]([NH:44][C:45]([NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[N:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:11][NH:12][C:13]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:19]

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 36945701,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidineHCID 865978712-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamate

생성물 1

HCID 178481900HCID 178481900, 화합물수율 77.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamate (1.58 g) in tetrahydrofuran (28 ml) was treated with 10% palladium on carbon (0.75 g) under a hydrogen atmosphere for 2 hours at room temperature. After the catalyst was filtered off, the filtrate was concentrated in vacuo to give a crude oil, which was dissolved in tetrahydrofuran (28 ml). To the solution were added triethylamine (2.04 ml) and di-tert-butyl ({[(trifluoromethyl)sulfonyl]imino}methylene)biscarbamate (2.86 g) successively at room temperature. The mixture was stirred at room temperature overnight. To the reaction mixture was added water to quench the reaction. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give di-tert-butyl {[((1S)-2-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-1-{[(tert-butoxycarbonyl)amino]methyl}-2-oxoethyl)amino]methylylidene}biscarbamate (1.53 g) as an amorphous solid.

후처리

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a crude oil, which
  4. customto quench
  5. customthe reaction
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f03c70a2ca544ebd8db8dd285dcf55f6
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192943B2

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