Diisopropylethylamine → HCID 86722063, 화합물

HRID 525046노트

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HRID 525046 반응식
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([Br:7])=[C:3]1[C:8]([NH:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)=[O:9].[CH2:19]([O:26][C@H:27]1[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:29]([C:39](O)=[O:40])[CH2:28]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C)C=O.O>[CH2:19]([O:26][C@H:27]1[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[C@H:29]([C:39](=[O:40])[NH:1][N:2]2[CH:6]=[CH:5][C:4]([Br:7])=[C:3]2[C:8](=[O:9])[NH:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)[CH2:28]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 11860409Boc-Hyp(Bzl)-OHHCID 70978853HCID 70978853, 화합물

생성물 1

HCID 86722063HCID 86722063, 화합물수율 74.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

1-Amino-3-bromo-N-(3,5-difluorophenyl)-1H-pyrrole-2-carboxamide (1.5 g, 4.75 mmol), (2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (0.99 g, 3.08 mmol) and diisopropylethylamine (2.8 ml, 16.08 mmol) were dissolved in dimethylformamide (30 ml) and the mixture cooled at 0° C. To this mixture, T3P (50% solution in ethyl acetate, 2.1 ml, 7.19 mmol) dissolved in DMF (5 ml) was dropwise added. Once the addition is over, the mixture was stirred at room temperature for 48 h. To this mixture, water was added and extracted twice with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate, filtered and the solvents evaporated under reduced pressure. The residue was purified by flash chromatography (0% to 25% hexanes/AcOEt) to yield 1.42 g (74% yield) of the title compound.

후처리

  1. additionwas dropwise added
  2. additionOnce the addition
  3. extractionextracted twice with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvents evaporated under reduced pressure
  8. customThe residue was purified by flash chromatography (0% to 25% hexanes/AcOEt)

출처 및 근거

ORD 기록
ord-76a02780c1864bdb86a2f29529021f95
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340547B2

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