Diisopropylethylamine → (S)-tert-Butyl 2-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate

HRID 524991노트

반응식

HRID 524991 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:49][N:50]1[CH:54]=[CH:53][CH:52]=[C:51]1[C:55]([NH:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:56]>CN(C)C=O>[C:58]1([NH:57][C:55]([C:51]2[N:50]([NH:49][C:13]([C@@H:9]3[CH2:10][CH2:11][CH2:12][N:8]3[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15])[CH:54]=[CH:53][CH:52]=2)=[O:56])[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 709224541-amino-N-phenyl-1H-pyrrole-2-carboxamide

생성물 1

HCID 70922354(S)-tert-Butyl 2-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(S)-1-(tert-Butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.80 g, 8.36 mmol) were dissolved in 20 ml of N,N-dimethylformamide and HATU (3.40 g, 8.95 mmol), DIEA (2.60 ml, 14.89 mmol) and 1-amino-N-phenyl-1H-pyrrole-2-carboxamide were added. The resulting solution was stirred at room temperature overnight and the solvent was removed in vacuum. The residue was taken up in ethyl acetate and the organic solution was washed with water and brine, dried over magnesium sulphate, filtered and evaporated to dryness. The crude product was purified by flash chromatography (0% to 30% hexane/AcOEt) to yield 1.90 g (62%) of the title compound as a white solid.

후처리

  1. customthe solvent was removed in vacuum
  2. washthe organic solution was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography (0% to 30% hexane/AcOEt)

출처 및 근거

ORD 기록
ord-cf3d02c3a6be41e89a3272e2846e4fdf
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340547B2

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