Triethylamine → N'-[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-N'-methyl-hydrazine carboxylic acid benzyl ester

HRID 34115

반응식

HRID 34115 반응식
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([OH:13])=O)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.Cl.[CH2:30]([O:37][C:38]([NH:40][NH:41][CH3:42])=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.O>[CH2:30]([O:37][C:38]([NH:40][N:41]([C:11](=[O:13])[CH2:10][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:9])[CH3:42])=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 24801390N'-methyl(benzyloxy)carbohydrazide hydrochloride

생성물 1

HCID 68932096N'-[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-N'-methyl-hydrazine carboxylic acid benzyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

2.1 g of (tert-butoxycarbonyl-methyl-amino)-acetic acid was dissolved in 150 mL of tetrahydrofuran, and 4.64 mL of triethylamine and 1.51 mL of isobutyl chloroformate were added under stirring at ice-cooling. After stirring at room temperature for 10 minutes, N′-methyl-hydrazine carboxylic acid benzyl ester hydrochloride was added and stirred at room temperature for 50 minutes. The reaction solution was added with water, extracted with ethyl acetate, and the resultant organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, followed by purification by silica gel column chromatography (ethyl acetate:n-hexane=1:1), to afford 3.2 g of N′-[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-N′-methyl-hydrazine carboxylic acid benzyl ester. Subsequently, by conducting catalytic hydrogen reduction in accordance with Production example 365, 1.9 g of the title compound was obtained.

후처리

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for 10 minutes
  3. stirringstirred at room temperature for 50 minutes
  4. extractionextracted with ethyl acetate
  5. washthe resultant organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customfollowed by purification by silica gel column chromatography (ethyl acetate:n-hexane=1:1)

출처 및 근거

ORD 기록
ord-3f5ffaef3d664f8ea002ee0785d41ddf
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429609B2

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