Monobasic potassium phosphate → methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate

HRID 1744106ノート

反応式

HRID 1744106 の反応式
[Br:1][C:2]1[C:3]([N:8](C(OCC(Cl)(Cl)Cl)=O)[C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][O:5][C:6]=1[CH3:7].OP([O-])(O)=O.[K+]>[Zn].C1COCC1>[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][O:5][C:6]=1[CH3:7]

参加物

5

反応物 2

HCID 516951Monobasic potassium phosphateHCID 69152129methyl N-(4-bromo-5-methylisoxazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

生成物 1

HCID 69152086methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a dry THF solution (20 mL) of methyl N-(4-bromo-5-methylisoxazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate (1.19 g, 2.47 mmol) and activated zinc (10.1 g, 154 mmol) was added ca. 10 mL of 1 M KH2PO4 (10 mmol) at 0° C. The mixture was stirred for 1.5 hours, filtered through celite, washed with 150 mL ethyl acetate, and concentrated to a small volume. The mixture was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, washed with brine, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography (20% ethyl acetate/hexane) to afford methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate.

後処理

  1. filtrationfiltered through celite
  2. washwashed with 150 mL ethyl acetate
  3. concentrationconcentrated to a small volume
  4. customThe mixture was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-0b8e3aed12184076909fe9851eebd254
出典データセット
uspto-grants-2006_03
特許番号
US07012075B2

反応ノート

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