4-Methoxybenzenesulfonyl chloride → 1-[(4-Methoxyphenyl)sulfonyl]-D-proline

HRID 264290

반응식

HRID 264290 반응식
[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([N:1]2[CH2:8][CH2:7][CH2:6][C@@H:2]2[C:3]([OH:5])=[O:4])(=[O:26])=[O:25])=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 8988D-Proline

생성물 1

HCID 7449021-[(4-Methoxyphenyl)sulfonyl]-D-proline

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(D)-proline (0.78 g, 6.77 mmol) is suspended in methylene chloride (25.0 mL). To this solution is added triethylamine (1.13 mL, 8.12 mmol) and 4-methoxybenzenesulfonyl chloride (1.4 g, 6.77 mmol), and the reaction is stirred at room temperature for two days. The reaction is then diluted with methylene chloride and washed successively with 1N hydrochloric acid, water, and brine. The organic phase is dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% methanol/ethyl acetate) to give 1-[4-methoxybenzenesulfonyl]-pyrrolidine-2(R)-carboxylic acid.

후처리

  1. washwashed successively with 1N hydrochloric acid, water, and brine
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customthe solvent is evaporated
  4. customThe product is purified by silica gel chromatography (10% methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-f54f586025c04cceb28d30155010910e
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646167

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