N-bromobutanimide → Tert-butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate

HRID 715970노트

반응식

HRID 715970 반응식
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]([CH3:39])([CH3:38])[C:11]([NH:13][C:14]1[C:15]([C:34]([O:36][CH3:37])=[O:35])=[C:16]([CH2:20][CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:17]=[CH:18][CH:19]=1)=[O:12]>C(#N)C>[Br:1][C:17]1[C:16]([CH2:20][CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])=[C:15]([C:34]([O:36][CH3:37])=[O:35])[C:14]([NH:13][C:11](=[O:12])[C:10]([CH3:39])([CH3:38])[CH3:9])=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 70984356Tert-butyl 2-{2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonyl-phenyl]-ethyl}-pyrrolidine-1-carboxylate2회

생성물 1

HCID 70982387Tert-butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate수율 78.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

N-Bromosuccinimide (1.24 g) was added to a solution of tert butyl 2-{2-[3-(2,2-dimethyl-propionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate (Intermediate 37, 2.74 g) in acetonitrile (40 mL) and the resultant mixture was stirred for 1 hour at room temperature. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25% to give tert butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate (2.55 g) as a colourless gum.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25%

출처 및 근거

ORD 기록
ord-2a727defd0414013b3aa24abdc6a35c3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187494B2

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