N-(tert-butoxycarbonyl)glycine → Ethyl 3-(2-{(tert-butoxycarbonyl)amino}acetylamino)propionate

HRID 394005ノート

反応式

HRID 394005 の反応式
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:10]([O:14][C:15]([NH:17][CH2:18][C:19](O)=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11]

参加物

7

反応物 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 21893946Ethyl 3-(2-{(tert-butoxycarbonyl)amino}acetylamino)propionate収率 75.1%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒2 回HCID 8471Triethylamine溶媒

実験手順

To a solution of 1.5 g of ethyl 3-aminopropionate monohydrochloride and 1.7 g of 2-{(tert-butoxycarbonyl)amino}acetic acid in 50 ml of chloroform, 1.6 g of 1-hydroxybenzotriazole monohydrate, 2.3 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride and 1.4 ml of triethylamine were added at room temperature by the order stated, and stirred for 2 hours at the same temperature. The reaction liquid was diluted with chloroform, and washed successively with saturated aqueous sodium bicarbonate solution, 10% aqueous citric acid solution and saturated saline solution, by the order stated, and dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/4) to provide 2.0 g of the title compound.

後処理

  1. customThe reaction liquid
  2. washwashed successively with saturated aqueous sodium bicarbonate solution, 10% aqueous citric acid solution and saturated saline solution, by the order
  3. dry with materialdried on anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/4)

出典と根拠

ORDレコード
ord-ccd09b6f84ba4a99937a316e7c400846
出典データセット
uspto-grants-2004_10
特許番号
US06809108B1

反応ノート

読み込み中…