Pyridine → HCID 59166761, 화합물

HRID 1442957노트

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HRID 1442957 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:33]([C:30]2[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=2)(=[O:35])=[O:34])[CH2:10][C@H:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 7408710Di-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

생성물 1

HCID 59166761HCID 59166761, 화합물수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester (CAS Reg. No. 170850-75-6) (1 g, 3.48 mmol) in 20 ml of CH2Cl2 was added pyridine (3.9 ml) and p-toluene sulphonyl chloride (0.7 g, 3.67 mmol) and the mixture stirred at room temperature under a nitrogen atmosphere for 72 hours. The solvent was removed under reduced pressure and the residue dissolved in EtOAc (100 ml) and washed with saturated citric acid solution (50 ml) then water (50 ml). The organic phase was dried (magnesium sulphate), filtered and evaporated under reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate:heptane (3:10) to give the title compound (1.5 g, 98%) as a colourless gum.

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (100 ml)
  3. washwashed with saturated citric acid solution (50 ml)
  4. dry with materialThe organic phase was dried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluting with ethyl acetate:heptane (3:10)

출처 및 근거

ORD 기록
ord-b9189b9c34154c4290a6134d7bfadb82
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659305B2

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