Dicyclohexylcarbodiimide → HCID 53849039, compound

HRID 1941305Notes

Reaction equation

HRID 1941305 reaction equation
[CH2:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([OH:15])=[O:14])[CH2:10][C:11]#[N:12])=[O:7])[CH2:2][CH2:3][CH3:4].[CH:16]1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C1COCC1.CO>[CH3:16][O:14][C:13](=[O:15])[C@@H:9]([CH2:10][C:11]#[N:12])[NH:8][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7]

Participants

6

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 53972361HCID 53972361, compound

Product 1

HCID 53849039HCID 53849039, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-butyloxycarbonyl-3-cyano-D-alanine (20.5 g, 97 mmol) and 4-dimethylaminopyridine (11.85 g, 97 mmol) in 150 mL THF and 33 mL methanol was added N,N'-dicyclohexylcarbodiimide (20 g, 97 mmol) and the solution was allowed to stir at room temperature for 2 hours. Insoluble material was removed by filtration and the solution was concentrated. The residue was taken up in ethyl acetate and the solution was washed with 5% citric acid, brine, NaHCO3 and brine, dried (MgSO4), and concentrated. Crystallization from ethyl acetate gave 18.8 g (85%) product. 1H-NMR: d (CDCl3) 5.48 (d, 1H); 4.54 (m, 1H); 3.84 (s, 3H); 2.98 (m, 2H); 1.44 (s, 9H). ES-MS: calcd M+1 229.2; found 229.0.

Workup

  1. customInsoluble material was removed by filtration
  2. concentrationthe solution was concentrated
  3. washthe solution was washed with 5% citric acid, brine, NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-80b33d9c3c894a34b860bd4162286c95
Source dataset
uspto-grants-1997_12
Patent number
US05703092

Reaction notes

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