4-Methylmorpholine → {(1S)-1-[N'-(4-Bromo-benzyl)-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid benzyl ester

HRID 1158505

반응식

HRID 1158505 반응식
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[Br:47][C:48]1[CH:56]=[CH:55][C:51]([CH2:52][NH:53][NH2:54])=[CH:50][CH:49]=1>CCOC(C)=O>[CH2:4]([O:3][C:1](=[O:2])[NH:11][C@H:12]([C:16]([NH:54][NH:53][CH2:52][C:51]1[CH:55]=[CH:56][C:48]([Br:47])=[CH:49][CH:50]=1)=[O:18])[CH:13]([CH3:14])[CH3:15])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 167731114-Bromobenzylhydrazine

생성물 1

HCID 11532141{(1S)-1-[N'-(4-Bromo-benzyl)-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid benzyl ester수율 79%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

Cbz-(L)-Valine (1.04 g, 4.14 mmol) was dissolved in EtOAc (50 mL) and EDAC (0.870 g, 4.54 mmol), HOBT (0.610 g, 4.51 mmol), and NMM (0.500 mL, 4.55 mmol) were added. The reaction mixture was stirred at room temperature for 30 min and then 4-bromo-benzylhydrazine (1.00 g, 4.97 mmol) in EtOAc (5 mL) was added and the stirring was continued for 2 h. After evaporation of the solvent, CHCl3 was added and the solution was washed with saturated NaHCO3 (aq.) and brine followed by drying (Na2SO4), filtration and evaporation of the organic solvent. The crude product was purified by column chromatography (silica, CHCl3/MeOH, 100:0-95:5) yielding the title compound (1.42 g, 79%) as a white solid.

후처리

  1. waitthe stirring was continued for 2 h
  2. customAfter evaporation of the solvent, CHCl3
  3. additionwas added
  4. washthe solution was washed with saturated NaHCO3 (aq.) and brine
  5. customby drying
  6. filtration(Na2SO4), filtration and evaporation of the organic solvent
  7. customThe crude product was purified by column chromatography (silica, CHCl3/MeOH, 100:0-95:5)

출처 및 근거

ORD 기록
ord-0df577dc0a4546529ac95ddd46b4284f
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807677B2

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