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

HRID 22968

反応式

HRID 22968 の反応式
[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]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 580181Dimethyl (2-oxoheptyl)phosphonateHCID 12132850HCID 12132850、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7e43c2d28ad343ca94099f5a921f4bc6
出典データセット
uspto-grants-2005_02
特許番号
US06849657B2

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