Sodium hydride → methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl] pyrrolidin-1-yl}ethyl)thio]-butanoate

HRID 22968

반응식

HRID 22968 반응식
[H-].[Na+].[O:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5]P(=O)(OC)OC.[CH:17]([C@H:19]1[CH2:23][CH2:22][C:21](=[O:24])[N:20]1[CH2:25][CH2:26][S:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=O>COCCOC>[O:24]=[C:21]1[CH2:22][CH2:23][C@H:19](/[CH:17]=[CH:5]/[C:4](=[O:3])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:20]1[CH2:25][CH2:26][S:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 580181Dimethyl (2-oxoheptyl)phosphonateHCID 12132850HCID 12132850, 화합물

생성물 1

HCID 12132851methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl] pyrrolidin-1-yl}ethyl)thio]-butanoate

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of sodium hydride (95%, 14 mg, 0.58 mmol) in 3 mL of anhydrous 1,2-dimethoxyethane at 0° C. under an argon atmosphere was added dimethyl 2-oxoheptylphosphonate (ACROS, 0.13 mL, 0.61 mmol). The cooling bath was removed and the reaction was stirred for 2 hours. After this time period, the mixture was cooled to 0° C. and a solution of methyl 4-({2-[(2R)-2-formyl-5-oxopyrrolidin-1-yl]ethyl}thio)butanoate (0.55 mmol) in anhydrous 1,2-dimethoxyethane was added. The reaction was allowed to come to room temperature, stirred for 2 hours and then quenched with an aqueous solution of saturated ammonium chloride. Ethyl acetate (50 mL) was then added and the mixture was partitioned between the two phases. The organic solution was dried (brine, Na2SO4), evaporated via reduced pressure and purified with column chromatography (SiO2, EtOAc/Hexane-1/1) to yield methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl]pyrrolidin-1-yl}ethyl)thio]-butanoate as an oil. This material was taken directly on to the next step.

후처리

  1. customThe cooling bath was removed
  2. customto come to room temperature
  3. stirringstirred for 2 hours
  4. customquenched with an aqueous solution of saturated ammonium chloride
  5. additionEthyl acetate (50 mL) was then added
  6. customthe mixture was partitioned between the two phases
  7. dry with materialThe organic solution was dried (brine, Na2SO4)
  8. customevaporated via reduced pressure
  9. custompurified with column chromatography (SiO2, EtOAc/Hexane-1/1)

출처 및 근거

ORD 기록
ord-7e43c2d28ad343ca94099f5a921f4bc6
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849657B2

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