Dicyclohexylcarbodiimide → N-(4-methoxycarbonyl-2-methylbutanoyl)-L-alanine benzyl ester

HRID 2419386Notes

Reaction equation

HRID 2419386 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH:7]([CH3:11])[C:8]([OH:10])=O)=[O:4].[CH2:12]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:12]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH:22][C:8](=[O:10])[CH:7]([CH3:11])[CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 726858benzyl (2S)-2-aminopropanoateHCID 131928974-Carbomethoxy-2-methylbutanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 22804619N-(4-methoxycarbonyl-2-methylbutanoyl)-L-alanine benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-methoxycarbonyl-2-methylbutanoic acid (3.1 g.), L-alanine benzyl ester (3.58 g.) and hydroxybenzotriazole (2.7 g.) are dissolved in dichloromethane. The solution is chilled in the ice bath and dicyclohexylcarbodiimide (4.12 g.) is added. After stirring 15 minutes in the ice bath and 18 hours at room temperature the precipitate is filtered off and the filtrate is concentrated to dryness. The residue is dissolved in ethyl acetate and washed neutral. The organic phase is dried over magnesium sulfate and concentrated to dryness to yield N-(4-methoxycarbonyl-2-methylbutanoyl)-L-alanine benzyl ester.

Workup

  1. additionis added
  2. filtrationis filtered off
  3. concentrationthe filtrate is concentrated to dryness
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed neutral
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e14e73650e804201820ae00318073f0b
Source dataset
uspto-grants-1978_08
Patent number
US04105789

Reaction notes

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