Diethyl 2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinate → (R)-1-ethyl hydrogen 3-t-butyloxycarbonylamino-3-ethoxycarbonylsuccinate

HRID 471349ノート

反応式

HRID 471349 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]([C:21]([O:23]CC)=[O:22])([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>P([O-])([O-])([O-])=O.C(#N)C>[C:1]([O:5][C:6]([NH:8][C@@:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])([C:21]([OH:23])=[O:22])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 1

HCID 86661708Diethyl 2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinate

生成物 1

HCID 86661709(R)-1-ethyl hydrogen 3-t-butyloxycarbonylamino-3-ethoxycarbonylsuccinate収率 108.4%

試薬・触媒・溶媒 2

HCID 1061Phosphate溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
30 °C

実験手順

1.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g), lyophilized product, product number: E3019] was dissolved in a 0.1 mol/L phosphate buffer adjusted to pH 7.5 (90 mL), and the solution was added with a solution of diethyl 2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinate (1.0 g) dissolved in acetonitrile (10 mL). The mixture was stirred at 30° C. for 4 hours to allow the reaction. After completion of the reaction, the reaction mixture was filtered by using a filtration aid (KC Floc 100) to remove the insoluble matter. The filtrate was cooled, and adjusted to pH 2 by adding 6 mol/L hydrochloric acid, then the objective substance was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (1.0 g).

後処理

  1. custom1.0 g of pig liver esterase produced by Sigma [PLE (27 kU/g), lyophilized product, product number: E3019]
  2. customthe reaction
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered
  5. customto remove the insoluble matter
  6. temperatureThe filtrate was cooled
  7. additionby adding 6 mol/L hydrochloric acid
  8. extractionthe objective substance was extracted with ethyl acetate
  9. washthe extract was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-9b95863783814cf4bb8cbd2728612d7f
出典データセット
uspto-grants-2014_01
特許番号
US08633001B2

反応ノート

読み込み中…