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

HRID 614883

반응식

HRID 614883 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-68bfb8aa63d5422f963f4c15209b9cb2
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04146641

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