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

HRID 1701365Notes

Reaction equation

HRID 1701365 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 yeild 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 to yeild N-(4-methoxycarbonyl-2-methylbutanoyl)-L-alanine benzyl ester

Sources & evidence

ORD record
ord-bf54d34fe2d141579b871167e03b5890
Source dataset
uspto-grants-1980_03
Patent number
US04192881

Reaction notes

Loading…