Dicyclohexylcarbodiimide → N-(3-methoxycarbonyl-2-methylpropanoyl)-L-alanine benzyl ester

HRID 614883ノート

反応式

HRID 614883 の反応式
[CH2:1]([O:8][C:9](=[O:13])[C@H:10]([CH3:12])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:39][O:40][C:41]([CH2:43][CH:44]([CH3:48])[C:45](O)=[O:46])=[O:42].COC(CC(=C)C(O)=O)=O>O1CCOCC1>[CH2:1]([O:8][C:9](=[O:13])[C@H:10]([CH3:12])[NH:11][C:45](=[O:46])[CH:44]([CH3:48])[CH2:43][C:41]([O:40][CH3:39])=[O:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 10868DicyclohexylcarbodiimideHCID 817914-Methyl hydrogen 2-methylenesuccinateHCID 726858benzyl (2S)-2-aminopropanoateHCID 45639014-Methoxy-2-methyl-4-oxobutanoic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 53826083N-(3-methoxycarbonyl-2-methylpropanoyl)-L-alanine benzyl ester

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

L-alanine benzyl ester (44.7 g.) and hydroxybenzotriazole (34 g.) are dissolved in dioxane (750 ml.) and the solution is chilled with stirring in an ice-water bath. Dicyclohexylcarbodiimide (51.5 g.) and 3-methoxycarbonyl-2-methylpropanoic acid (36 g.), prepared by hydrogenation of 3-methoxycarbonyl-2-methylene propanoic acid, are added in that order and the mixture is stirred at room temperature for 18 hours. The precipitate is filtered off, and the filtrate is concentrated to dryness in vacuo. The residue is dissolved in ethyl acetate and washed neutral. The ethyl acetate is dried over magnesium sulfate and concentrated to dryness in vacuo to yield N-(3-methoxycarbonyl-2-methylpropanoyl)-L-alanine benzyl ester.

後処理

  1. temperaturethe solution is chilled
  2. additionare added in that order
  3. stirringthe mixture is stirred at room temperature for 18 hours
  4. filtrationThe precipitate is filtered off
  5. concentrationthe filtrate is concentrated to dryness in vacuo
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washwashed neutral
  8. dry with materialThe ethyl acetate is dried over magnesium sulfate
  9. concentrationconcentrated to dryness in vacuo

出典と根拠

ORDレコード
ord-68bfb8aa63d5422f963f4c15209b9cb2
出典データセット
uspto-grants-1979_03
特許番号
US04146641

反応ノート

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