Dicyclohexylcarbodiimide → HCID 23318057, compound

HRID 1981896Notes

Reaction equation

HRID 1981896 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:16]([OH:18])=O)[CH2:10][CH2:11][S:12][CH2:13][CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].OC1CC(=O)NC1=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][CH2:11][S:12][CH2:13][CH2:14][NH:15][C:16]1=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 181836963-Hydroxypyrrolidine-2,5-dioneHCID 23318048HCID 23318048, compound

Product 1

HCID 23318057HCID 23318057, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-t-Butoxycarbonyl-S-(2-aminoethyl)-D,L-homocysteine (0.1 g) and hydroxysuccinimide (0.044 g) are dissolved in 4 ml of DMF. Dicyclohexylcarbodiimide (0.086 g) in 1 ml of DMF is added dropwise. After 4 days at room temperature, the reaction mixture is filtered, and then lyophilized. The residue is taken up in methylene chloride. Again insoluble white solid is removed by filtration. The crude product is chromatographed on silica gel (20:1 chloroform-methanol) to afford the product as a white solid (0.02 g). The NMR spectrum (in MeOH-d4) shows a multiplet between 4.4 and 4.8, a multiplet between 3.2 and 3.4, complex absorptions between 2.2 and 2.7, and between 1.5 and 1.9, and a singlet at 1.2.

Workup

  1. filtrationthe reaction mixture is filtered
  2. customAgain insoluble white solid is removed by filtration
  3. customThe crude product is chromatographed on silica gel (20:1 chloroform-methanol)

Sources & evidence

ORD record
ord-c2000fb6a25d4a96941c8bd04759dca9
Source dataset
uspto-grants-1986_06
Patent number
US04594341

Reaction notes

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