Benzyl carbazate → N'-[2-(tert-Butoxycarbonyl-methyl-amino)-acetyl]-hydrazine Carboxylic Acid Benzyl Ester

HRID 34052

反応式

HRID 34052 の反応式
[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:21][C:22]([NH:24][NH2:25])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH2:14]([O:21][C:22]([NH:24][NH:25][C:10](=[O:12])[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:13])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

8

反応物 5

HCID 79242Benzyl carbazateHCID 81531DiisopropylethylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 59796921N'-[2-(tert-Butoxycarbonyl-methyl-amino)-acetyl]-hydrazine Carboxylic Acid Benzyl Ester収率 88%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

6.95 g of 2-(tert-butoxycarbonyl-methyl-amino)-acetic acid, 6.1 g of hydrazine carboxylic acid benzyl ester, 6.18 g of 1-hydroxybenzotriazole monohydrate and 19.2 mL of N,N-diisopropylethylamine were dissolved in 120 mL of N,N-dimethylformamide, and 10.6 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under stirring at room temperature. After stirring at room temperature for 17 hours, the reaction solution was added with water and 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 (hexane:ethyl acetate=1:1), to obtain 10.9 g of the title compound.

後処理

  1. stirringAfter stirring at room temperature for 17 hours
  2. extractionextracted with ethyl acetate
  3. washthe resultant organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customfollowed by purification by silica gel column chromatography (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-7308ab218bc44c31ba569428a619ac05
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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