Dicyclohexylcarbodiimide → HCID 178479473, compound

HRID 358266

Reaction equation

HRID 358266 reaction equation
[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4].O[C:17]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:19][C:18]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][C:30]2[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=2)[C:18]2[O:19][C:20]3[C:25]([C:26](=[O:27])[CH:17]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:14])[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11349FlavonolHCID 178479474HCID 178479474, compound

Product 1

HCID 178479473HCID 178479473, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 9.89 g of trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride, 10.1 g of 3-hydroxyflavon and 8.66 g of dicyclohexylcarbodiimide was added to 100 ml of dry pyridine, and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered to remove any insoluble materials which were washed with pyridine. The filtrate and the washing were combined and evaporated. 0.1N hydrochloric acid was added to the residue, and the mixture was washed with ethyl acetate. The aqueous layer was concentrated to 30 ml and allowed to stand overnight in a refrigerator to obtain 1 g of 3'-flavonyl trans-4-guanidinomethylcyclohexanecarboxylate hydrochloride as colorless needles having a melting point of 201°-203° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove any insoluble materials which
  3. washwere washed with pyridine
  4. customevaporated
  5. addition0.1N hydrochloric acid was added to the residue
  6. washthe mixture was washed with ethyl acetate
  7. concentrationThe aqueous layer was concentrated to 30 ml
  8. waitto stand overnight in a refrigerator

Sources & evidence

ORD record
ord-7c349e4ebb7b407ebf4351ff1f3fb8a9
Source dataset
uspto-grants-1984_08
Patent number
US04465851

Linked notes

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