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4-Toluenesulfonyl chloride → N-tert-Butoxycarbonyl-cis-4-(p-Toluenesulfonyloxy)-D-Proline Methyl Ester

HRID 2185415
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HRID 2185415 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14](=[O:28])[C@H:15]1[CH2:19][C@@H:18]([OH:20])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:12][O:13][C:14](=[O:28])[C@H:15]1[CH2:19][C@@H:18]([O:20][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 6951202(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

생성물 1

HCID 13425770N-tert-Butoxycarbonyl-cis-4-(p-Toluenesulfonyloxy)-D-Proline Methyl Ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

4-Dimethylaminopyridine (1.21 g) and p-toluenesulfonyl chloride (1.51 g) were added to a solution of N-tert-butoxycarbonyl-cis-4-hydroxy-D-proline methyl ester (A, 971 mg) in dichloromethane (20 mL). After stirrng at room temperature for 4 hr, the solvent was removed in vacuo. The residue was diluted with ethyl acetate, and washed with 10% citric acid, water, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform then chloroform:ethyl acetate=1:50, v/v) to give the title compound (1.65 g) as a colorless oil.

후처리

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 10% citric acid, water, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform

출처 및 근거

ORD 기록
ord-69920ede65644d28adbf8517628fbcb8
출처 데이터셋
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06399629B1

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