Trifluoroacetic acid → (3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid Ethyl Ester

HRID 1163350노트

반응식

HRID 1163350 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH3:2].C(O[CH2:23][N:24]([CH2:32][Si](C)(C)C)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)CCCC.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C@H:5]1[C@@H:6]([CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:32][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23]1)=[O:16])[CH3:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 5463862-Butenoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, ethyl esterHCID 10902461N-[(pentyloxy)methyl]-N-[(trimethylsilyl)-methyl]-benzenemethanamine

생성물 1

HCID 68420071(3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid Ethyl Ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2 g of 4-tert-butoxycarbonylamino-but-2-enoic acid ethyl ester (8.72 mmol) and 5.12 g N-[(pentyloxy)methyl]-N-[(trimethylsilyl)methyl]-benzene-methanamine (17.4 mmol) in 50 ml dichloromethane was added 10 micro-l. trifluoroacetic acid. The reaction was monitored by TLC. The reaction was complete after 10 min. The mixture was diluted with dichloromethane, washed with sat. sodium bicarbonate solution and brine, dried over Mg sulfate, filtered and the filtrate evaporated. The residue was purified by filtration over a short silica column, using a 7/3 hexane/ethyl acetate mixture as eluent.

후처리

  1. washwashed with sat. sodium bicarbonate solution and brine
  2. dry with materialdried over Mg sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. filtrationThe residue was purified by filtration over a short silica column

출처 및 근거

ORD 기록
ord-4326f11222d64a129b129976b683fa56
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820823B2

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