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

HRID 614866Notes

Reaction equation

HRID 614866 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-01a02a29d308472eb399c818f8e8993f
Source dataset
uspto-grants-1979_03
Patent number
US04146639

Reaction notes

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