Ethyl Acetate → HCID 10742597, compound

HRID 2260159Notes

Reaction equation

HRID 2260159 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[C:25]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:26][C:27]([O-])=[O:28].C1(N=C=NC2CCCCC2)CCCCC1.C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH3:22][C:21]([CH3:24])([O:20][C:18]([N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:27](=[O:28])[CH2:26][C:25]([O:31][CH2:32][CH3:33])=[O:30])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])=[O:19])[CH3:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 3595298Propanedioic acid, monoethyl esterHCID 10904092N1,N4-Bis-Boc-spermidine

Product 1

HCID 10742597HCID 10742597, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

After stirring for 0.5 hour, a solution of 1.04 g (3×10-3 mol) of 1,1-dimethylethyl 10-amino-6-[(1,1-dimethylethoxy)carbonyl]-2,6-diazadecanoate in 5 ml of anhydrous chloroform is added dropwise at 0° C. The mixture is stirred for 5 hours at room temperature and 1.06 g (8×10-3 mol) of ethyl malonate and 1.64 g (8×10-3 mol) of 1,3-dicyclohexylcarbodiimide are added. The mixture is stirred for 1 hour and the solvent is evaporated off under reduced pressure. The pasty residue obtained is chromatographed on silica using an ethyl acetate/hexane mixture (1/1 v/v) and then ethyl acetate as the eluent to give 0.95 g (yield: 69%) of the expected product in the form of an oil.

Workup

  1. stirringThe mixture is stirred for 5 hours at room temperature
  2. stirringThe mixture is stirred for 1 hour
  3. customthe solvent is evaporated off under reduced pressure
  4. customThe pasty residue obtained
  5. customis chromatographed on silica using an ethyl acetate/hexane mixture (1/1 v/v)

Sources & evidence

ORD record
ord-9d79426ac265499b96fad3ee67b99c10
Source dataset
uspto-grants-1995_12
Patent number
US05476870

Reaction notes

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