Dicyclohexylcarbodiimide → HCID 86749041, compound

HRID 2210480Notes

Reaction equation

HRID 2210480 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C@H:4]([CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)[NH2:5].[OH:20][N:21]=[C:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23](O)=[O:24].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[CH3:1][O:2][C:3](=[O:19])[C@H:4]([CH2:6][C:7]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1)[NH:5][C:23](=[O:24])[C:22](=[N:21][OH:20])[CH2:26][CH:27]([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 54157075HCID 54157075, compoundHCID 573586802-(Hydroxyimino)-4-methylpentanoic acid

Product 1

HCID 86749041HCID 86749041, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 34.47 g of 3,4,5-trimethoxyphenylalanine methyl ester, 18.87 g of α-hydroxyiminoisocaproic acid, 14.96 g of N-hydroxysuccinimide in 1 liter of dioxane, was added 26.82 g of N,N'-dicyclohexylcarbodiimide, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was filtrated, and the filtrate was subjected to distillation to remove the solvent. The resulting residue was purified by means of a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:2) to obtain 42.70 g of N-(2-hydroxyimino-4-methylpentanoyl)-(3,4,5-trimethoxy)phenylalanine methyl ester.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. distillationthe filtrate was subjected to distillation
  3. customto remove the solvent
  4. customThe resulting residue was purified by means of a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-6e27ba47ee7f4263b70a9a588379cb2e
Source dataset
uspto-grants-1995_10
Patent number
US05459142

Reaction notes

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