Dicyclohexylcarbodiimide → 4-Amidino-2-benzoylphenyl 3-benzyloxycarbonylaminopropionate

HRID 1981413Notes

Reaction equation

HRID 1981413 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:37]1[CH:42]=[CH:41][C:40]([C:43](=[NH:45])[NH2:44])=[CH:39][C:38]=1[C:46](=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][C:37]1[CH:42]=[CH:41][C:40]([C:43](=[NH:44])[NH2:45])=[CH:39][C:38]=1[C:46](=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 540991824-Amidino-2-benzoylphenol methanesulfonate

Product 1

HCID 131784404-Amidino-2-benzoylphenyl 3-benzyloxycarbonylaminopropionateYield 59.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 50 ml of anhydrous pyridine, was dissolved 3.3 g of 3-benzyloxycarbonylaminopropionic acid. To the solution, while being cooled in ice, was added 3.7 g of DCC. The mixture was stirred for 30 minutes. After addition of 5.0 g of 4-amidino-2-benzoylphenol methanesulfonate, the mixture was further stirred overnight. The precipitate which was formed was separated by filtration and washed with pyridine. Ethyl ether was added to the filtrate to separate an oily substance which solidified upon stirring. The solidified substance was collected by filtration, washed with ethyl ether, and dissolved in DMF. The crystals precipitated out of the DMF solution by the addition of ethyl ether were recrystallized from ethanol to yield 3.9 g of colorless granular crystals of 4-amidino-2-benzoylphenyl 3-benzyloxycarbonylaminopropionate methanesulfonate.

Workup

  1. temperatureTo the solution, while being cooled in ice
  2. waitthe mixture was further stirred overnight
  3. customThe precipitate which was formed
  4. customwas separated by filtration
  5. washwashed with pyridine
  6. additionEthyl ether was added to the filtrate
  7. customto separate an oily substance which
  8. stirringupon stirring
  9. filtrationThe solidified substance was collected by filtration
  10. washwashed with ethyl ether
  11. dissolutiondissolved in DMF
  12. customThe crystals precipitated out of the DMF solution by the addition of ethyl ether
  13. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-3a312c2fa523433fbefcab88fcc70cea
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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