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

HRID 34115

反応式

HRID 34115 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3f5ffaef3d664f8ea002ee0785d41ddf
出典データセット
uspto-grants-2008_09
特許番号
US07429609B2

関連ノート

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