Dicyclohexylcarbodiimide → HCID 178498200, compound

HRID 1589477Notes

Reaction equation

HRID 1589477 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O)(=O)=O.[C:42]([C:45]1[CH:54]=[C:49]([C:50]([O:52][CH3:53])=[O:51])[C:48](O)=[CH:47][CH:46]=1)(=[NH:44])[NH2:43]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([O:21][C:48]2[CH:47]=[CH:46][C:45]([C:42](=[NH:43])[NH2:44])=[CH:54][C:49]=2[C:50]([O:52][CH3:53])=[O:51])=[O:20])[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 136387255HCID 136387255, compoundHCID 178523389HCID 178523389, compound

Product 1

HCID 178498200HCID 178498200, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 40 ml of anhydrous pyridine, was dissolved 4.3 g of trans-4-benzyloxycarbonylaminomethylcyclohexanecarboxylic acid. To the solution, while being cooled in ice, was added 3.7 g of DCC. To the mixture which had been stirred for 30 minutes, was added 4.1 g of methyl 5-amidinosalicylate methanesulfonate. The mixture was stirred overnight at room temperature. The precipitate which was formed was separated by filtration and washed with pyridine. Ethyl ether was added to the filtrate and the precipitated white crystals were washed with ethyl ether and dissolved in DMF. The colorless crystals separated from the DMF solution by the addition of ethyl ether were recrystallized from ethanol to obtain 4.3 g of a colorless powder of 4-amidino-2-methoxycarbonylphenyl trans-4-benzyloxycarbonylamino-methylcyclohexanecarboxylate methanesulfonate.

Workup

  1. temperatureTo the solution, while being cooled in ice
  2. stirringThe mixture was stirred overnight at room temperature
  3. customThe precipitate which was formed
  4. customwas separated by filtration
  5. washwashed with pyridine
  6. additionEthyl ether was added to the filtrate
  7. washthe precipitated white crystals were washed with ethyl ether
  8. dissolutiondissolved in DMF
  9. customThe colorless crystals separated from the DMF solution by the addition of ethyl ether
  10. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-41c1065394f54169960cea6f4262cafb
Source dataset
uspto-grants-1986_02
Patent number
US04570006

Reaction notes

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