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

HRID 1744114노트

반응식

HRID 1744114 반응식
[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

참가 물질

5

반응물 2

HCID 516951Monobasic potassium phosphate2회HCID 691523624-methoxybenzyl N-(4-bromo-1-methyl-1H-pyrazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-02bb2e8239f34110b4b4353ad661635b
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07012075B2

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