Monobasic potassium phosphate → 4-methoxybenzyl N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucinate

HRID 1744114ノート

反応式

HRID 1744114 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][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][N:5]([CH3:7])[CH:6]=1.OP([O-])(O)=O.[K+]>C1COCC1.[Zn]>[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][N:5]([CH3:7])[CH:6]=1

参加物

5

反応物 2

HCID 516951Monobasic potassium phosphate2 回HCID 691523624-methoxybenzyl N-(4-bromo-1-methyl-1H-pyrazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

生成物 1

HCID 691531674-methoxybenzyl N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucinate

試薬・触媒・溶媒 2

HCID 23994Zinc触媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To 4-methoxybenzyl N-(4-bromo-1-methyl-1H-pyrazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate (1.72 g, 2.89 mmol) in dry THF (50 mL) was added activated zinc powder (1.89 g, 28.9 mmol) followed by an aqueous solution of KH2PO4 (1.0 M, 5.8 mL, 11.6 mmol) and the reaction mixture was stirred for ½ hour. Additional aliquots of activated zinc powder (950 mg, 14.45 mmol) and aqueous solution of KH2PO4 (1.0 M, 2.9 mL, 2.9 mmol) were added and the reaction mixture stirred for 1½ hour. The zinc powder was filtered off, rinsed with Et2O and water and the product extracted with ether (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 25/75, then 3/7) to afford 4-methoxybenzyl N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucinate.

後処理

  1. stirringthe reaction mixture stirred for 1½ hour
  2. filtrationThe zinc powder was filtered off
  3. washrinsed with Et2O and water
  4. extractionthe product extracted with ether (2×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography over silica gel (EtOAc/Hex, 25/75

出典と根拠

ORDレコード
ord-02bb2e8239f34110b4b4353ad661635b
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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