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Dimethylformamide → N-Boc-trans-4-tosyloxy-L-proline methyl ester

HRID 490570
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인쇄 미리보기

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HRID 490570 반응식
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.CN(C=O)C>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3]([CH:4]1[CH2:8][CH:7]([O:9][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:18])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[O:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 73974-Toluenesulfonyl chlorideHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

생성물 1

HCID 13425771N-Boc-trans-4-tosyloxy-L-proline methyl ester

시약·촉매·용매 2

HCID 1049Pyridine용매
HCID 6344
Dichloromethane
용매

실험 절차

To a solution of trans-N-Boc-4-hydroxy-L-proline methyl ester (7) in pyridine and dry DCM at 0° C. is added 4-methyl-benzenesulfonyl chloride. After adding, the mixture is refluxed overnight. The solvent is evaporated and then the residue is dissolved in CH2Cl2. After removal of solvent, the crude 4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester is obtained, which is used in the following reaction without further purification. To a solution of 4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester thus obtained above in dry DMF is added NaN3 in one portion, and the reaction mixture is stirred at about 50° C. for 5 h. The resulting mixture is purified to give 4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (8).

후처리

  1. additionAfter adding
  2. temperaturethe mixture is refluxed overnight
  3. customThe solvent is evaporated
  4. dissolutionthe residue is dissolved in CH2Cl2
  5. customAfter removal of solvent
  6. customthe crude 4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester is obtained
  7. customwhich is used in the following reaction without further purification

출처 및 근거

ORD 기록
ord-9c15454bdc8c42888c4c4ab6537db2ab
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07528136B2

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