Dicyclohexylcarbodiimide → HCID 13178480, compound

HRID 1981446Notes

Reaction equation

HRID 1981446 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH: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[C:42]1[CH:47]=[CH:46][C:45]([C:48](=[NH:50])[NH2:49])=[CH:44][C:43]=1[O:51][CH3:52])(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:42]2[CH:47]=[CH:46][C:45]([C:48](=[NH:49])[NH2:50])=[CH:44][C:43]=2[O:51][CH3:52])=[O:18])=[CH:20][CH:21]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14799974-((((Benzyloxy)carbonyl)amino)methyl)benzoic acidHCID 54016649HCID 54016649, compound

Product 1

HCID 13178480HCID 13178480, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3.7 g of 4-benzyloxycarbonylaminomethylbenzoic acid in 40 ml of dried pyridine, was added 3.1 g of DCC with cooling in ice. The mixture was stirred for 30 minutes. After addition of 3.1 g of 4-amidino-2-methoxyphenol methanesulfonate, the mixture was further stirred overnight at room temperature. The reaction mixture was removed of the insolubles and mixed with ethyl ether to precipitate a colorless solid substance which on recrystallization from a methanolethyl ether mixture gave 3.2 g of colorless crystals of 4-amidino-2-methoxyphenyl 4-benzyloxycarbonylaminomethylbenzoate methanesulfonate.

Workup

  1. temperaturewith cooling in ice
  2. waitthe mixture was further stirred overnight at room temperature
  3. customThe reaction mixture was removed of the insolubles
  4. additionmixed with ethyl ether
  5. customto precipitate a colorless solid substance which
  6. customon recrystallization from a methanolethyl ether mixture

Sources & evidence

ORD record
ord-b54ac14cdd794c42ad684b648d8115f1
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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