Dicyclohexylcarbodiimide → HCID 54392109, compound

HRID 2226578Notes

Reaction equation

HRID 2226578 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:19][C:20](=[O:27])[C@@H:21]([OH:26])[CH2:22][S:23][CH2:24][CH3:25])[CH:17]=[CH2:18].[C:28]([S:31][CH2:32][C@@H:33]([CH3:37])[C:34](O)=[O:35])(=[O:30])[CH3:29]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:16]([O:19][C:20](=[O:27])[C@@H:21]([O:26][C:34](=[O:35])[C@H:33]([CH3:37])[CH2:32][S:31][C:28](=[O:30])[CH3:29])[CH2:22][S:23][CH2:24][CH3:25])[CH:17]=[CH2:18]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2724506D-beta-acetylthioisobutyric acidHCID 54445895HCID 54445895, compound

Product 1

HCID 54392109HCID 54392109, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Dicyclohexylcarbodiimide (1.13 g, 5.5 mmol) in dichloromethane (20 ml) was added to a stirred solution of the product of step b) (0.95 g, 5 mmol), (S)-3-(Acetylthio)-2-methylpropanoic acid (0.81 g, 5 mmol) and 4-(dimethylamino)pyridine (0.06 g, 0.5 mmol) in dichloromethane (30 ml). The mixture was stirred overnight, filtered and the solvent evaporated. The residue was dissolved in ethyl acetate, filtered and washed with potassium hydrogen sulphate solution, sodium bicarbonate solution and brine and the solvent evaporated. Chromatography on silica with ethyl acetate/petroleum ether as eluant gave the sub-title compound (1.1 g).

Workup

  1. filtrationfiltered
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationfiltered
  5. washwashed with potassium hydrogen sulphate solution, sodium bicarbonate solution and brine
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-8b1b3af61f6b4e1c9f3c3e7d4ac9d1ba
Source dataset
uspto-grants-1994_09
Patent number
US05348978

Reaction notes

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