Dicyclohexylcarbodiimide → HCID 86747153, compound

HRID 2255163Notes

Reaction equation

HRID 2255163 reaction equation
[NH2:1][CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].O[CH:14]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:15](O)=[O:16].[OH:22][N:23]1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[OH:22][N:23]=[C:14]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:15]([NH:1][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:16]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 81272Propanedioic acid, 2-amino-, 1,3-diethyl ester2×HCID 92779(+-)-2-Hydroxyisocaproic acid

Product 1

HCID 86747153HCID 86747153, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

30 Milliliters of water and 7.0 g of sodium hydrogen carbonate were added to a suspension of 17.5 g of diethyl aminomalonate hydrochloride in 150 ml of dichloromethane. After 20 minutes, the dichloromethane layer was separated and dried over magnesium sulfate. The solvent was removed by evaporation under reduced pressure to obtain colorless oily diethyl aminomalonate. The diethyl aminomalonate was made into a solution of the diethyl aminomalonate, 10.0 g of α-hydroxyisocaproic acid and 8.7 g of N-hydroxysuccinimide dissolved in 200 ml of dioxane. To the solution was added 15.7 g of N,N'-dicyclohexylcarbodiimide. The mixture was stirred for 16 hours at room temperature and then filtered. The filtrate was subjected to removal of the solvent by evaporation. The residue was mixed with ethyl acetate, and the mixture was washed with 10% hydrochloric acid, water, an aqueous solution saturated with sodium hydrogen carbonate, and an aqueous solution saturated with NaCl solution in this order, and dried over magnesium sulfate. The solvent was removed by evaporation to obtain 29.19 g of diethyl N-(2-hydroxyimino- 4-methylpentanoyl)aminomalonate (Compound B-25) as a colorless oily substance.

Workup

  1. filtrationfiltered
  2. customThe filtrate was subjected to removal of the solvent by evaporation
  3. additionThe residue was mixed with ethyl acetate
  4. washthe mixture was washed with 10% hydrochloric acid, water
  5. dry with materialan aqueous solution saturated with sodium hydrogen carbonate, and an aqueous solution saturated with NaCl solution in this order, and dried over magnesium sulfate
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-ef31f401088a47ffb34818fdf6261a76
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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