Dicyclohexylcarbodiimide → HCID 15679351, compound

HRID 1647386Notes

Reaction equation

HRID 1647386 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2].Cl.[CH2:16]([O:18][C:19](=[O:30])[C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25](=[O:29])[C@H:26]([CH3:28])[NH2:27])[CH3:17].C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[CH2:16]([O:18][C:19](=[O:30])[C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25](=[O:29])[C@H:26]([CH3:28])[NH:27][C:12]([C:10]1[N:11]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[CH:8][CH:9]=1)=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 35944446-(Ethoxycarbonyl)picolinic acidHCID 15927166L-alanyl-L-proline ethyl ester hydrochloride

Product 1

HCID 15679351HCID 15679351, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 4.31 g (0.022 mol) of 6-ethoxycarbonyl-2-pyridinecarboxylic acid in 100 ml of anhydrous pyridine, there are added 5.5 g (0.022 mol) of L-alanyl-L-proline ethyl ester hydrochloride and 4.6 g of N,N'-dicyclohexyl carbodiimide. Stirring is continued for 20 minutes at room temperature, and the bulky precipitate of dicyclohexyl urea is filtered and washed with acetone. The solvent from the filtrate and washings is distilled off under reduced pressure and the crude product obtained is purified by column chromatography over silica gel using chloroform:acetone (10:1) as eluant. The isolated solid is crystallized from an acetone/isopropyl ether/petroleum ether mixture, to give 4.27 g of the desired product as acicular crystals (yield: 53%).

Workup

  1. filtrationthe bulky precipitate of dicyclohexyl urea is filtered
  2. washwashed with acetone
  3. distillationThe solvent from the filtrate and washings is distilled off under reduced pressure
  4. customthe crude product obtained
  5. customis purified by column chromatography over silica gel
  6. customThe isolated solid is crystallized from an acetone/isopropyl ether/petroleum ether mixture

Sources & evidence

ORD record
ord-35e68b0c0f494dffb8db1f8645756a6b
Source dataset
uspto-grants-1995_07
Patent number
US05432159

Reaction notes

Loading…