Triethylamine → HCID 18646450, compound

HRID 2248066Notes

Reaction equation

HRID 2248066 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.CCN(CC)CC.[CH3:42][O:43][C:44](=[O:61])[CH2:45][NH:46][C:47](=[O:60])[C@H:48]([CH:55]([CH3:59])[CH:56]=C=O)[NH:49]OC(C)(C)C>C(Cl)Cl.CN(C=O)C>[CH3:42][O:43][C:44](=[O:61])[CH2:45][NH:46][C:47](=[O:60])[C@H:48]([CH:55]([CH3:56])[CH3:59])[NH:49][C:17](=[O:19])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 10868DicyclohexylcarbodiimideHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 86744972HCID 86744972, compound

Product 1

HCID 18646450HCID 18646450, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-benzyloxycarbonyl-L-leucine (2.65 g, 10 mmol) in 15 ml CH2Cl2 was cooled in an ice-water bath and stirred with a magnetic stirrer. A solution of dicyclohexylcarbodiimide (2.58 g, 12.5 mmol) in CH2Cl2 was added, and stirring was continued for 15 minutes. Dicyclohexylurea was filtered. The solvent was evaporated in vacuo or at room temperature. The residue was dissolved in 4 ml DMF(1) and cooled in an ice-water bath. CF3CO2H·H-Val-Gly-OMe(1.51 g, 5 mmol) was dissolved in 7 ml DMF, and Et3N (0.25 g =0.34 ml, 2.5 mmol) was added, whereupon the mixture was added to the solution (1) and Et3N (0.34 ml) was again added. Stirring was continued for 24 hours at room temperature. The reaction mixture was filtered, diluted with water and AcOEt and separated. The water layer was extracted twice with AcOEt. Collected organic phases were washed once with water, once with 0.5M NaHCO3, once with water, once with 1N HCl, and twice with water and dried over anhydrous MgSO4. After filtration the solvent was evaporated in vacuo. The solid residue was triturated with petroleum ether, filtered and dried in vacuo.

Workup

  1. stirringstirring
  2. filtrationDicyclohexylurea was filtered
  3. customThe solvent was evaporated in vacuo or at room temperature
  4. dissolutionThe residue was dissolved in 4 ml DMF(1)
  5. temperaturecooled in an ice-water bath
  6. additionwas again added
  7. stirringStirring
  8. waitwas continued for 24 hours at room temperature
  9. filtrationThe reaction mixture was filtered
  10. additiondiluted with water and AcOEt
  11. customseparated
  12. extractionThe water layer was extracted twice with AcOEt
  13. washCollected organic phases were washed once with water, once with 0.5M NaHCO3, once with water, once with 1N HCl
  14. dry with materialtwice with water and dried over anhydrous MgSO4
  15. filtrationAfter filtration the solvent
  16. customwas evaporated in vacuo
  17. customThe solid residue was triturated with petroleum ether
  18. filtrationfiltered
  19. customdried in vacuo

Sources & evidence

ORD record
ord-f0ff7943f10a40beb31a13ad515d3c5e
Source dataset
uspto-grants-1991_08
Patent number
US05037957

Reaction notes

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