Diisopropylethylamine → 2-[1-(4-Bromo-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 71685

반응식

HRID 71685 반응식
C(N(CC)C(C)C)(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH:19](C(O)=O)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CN([C:28]([O:32]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:49]([O:51][C:52](=[O:63])[C:53]([NH2:62])([C:55]1[CH:60]=[CH:59][C:58]([Br:61])=[CH:57][CH:56]=1)[CH3:54])[CH3:50]>CN(C=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH2:20][CH:21]1[C:28](=[O:32])[NH:62][C:53]([C:55]1[CH:56]=[CH:57][C:58]([Br:61])=[CH:59][CH:60]=1)([C:52]([O:51][CH2:49][CH3:50])=[O:63])[CH3:54])=[O:16])([CH3:11])([CH3:12])[CH3:13]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acidHCID 3494252Ethyl 2-amino-2-(4-bromophenyl)propanoateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 666204492-[1-(4-Bromo-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester수율 58.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N,N-diisopropylethylamine (4.1 mL, 23.6 mmol) was added dropwise to a mixture of pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (0.7 g, 3.2 mmol), HATU (1.2 g, 3.2 mmol) and 2-amino-2-(4-bromo-phenyl)-propionic acid ethyl ester (0.8 g, 2.9 mmol) in DMF (20 mL), and stirred at ambient condition for 3 hours. Most of the volatile component was removed in vacuo, and the resulting residue was dissolved in ethyl acetate (150 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product as a colorless oil (0.8 g, 58%). m/z 490.9, 492.9 (M+Na)+.

후처리

  1. customMost of the volatile component was removed in vacuo
  2. dissolutionthe resulting residue was dissolved in ethyl acetate (150 mL)
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-d26cd7743c354e00a867d948ff49cd64
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822430B2

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