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

HRID 272060ノート

反応式

HRID 272060 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 distlled 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. 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-28d8bbf7aa594d1590bdccfe5212e611
出典データセット
uspto-grants-2008_11
特許番号
US07452908B2

反応ノート

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