Dicyclohexylcarbodiimide → HCID 12802599, compound

HRID 1156945Notes

Reaction equation

HRID 1156945 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[O:4].Cl.[NH:7]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@H:8]([C:16](O)=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>O.CN(C=O)C>[NH:7]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@H:8]([C:16]([NH:1][NH:2][C:3]([NH2:5])=[O:4])=[O:17])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11236Semicarbazide hydrochlorideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione

Product 1

HCID 12802599HCID 12802599, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 5 ml of water is dissolved 2.50 g (22 mM) of NH2NHCONH2.HCl, the solution is neutralized with 3.14 ml of TEA, and 40 ml of DMF is added. To this solution are added 3.0 g of Z-Phe-OH, 2.0 g of HONB and 2.3 g of DCC. The mixture is stirred for 24 hours, the precipitated DCU filtered off, the solvent distilled off and the residue dissolved in 200 ml of ethyl acetate. The solution is washed with aqueous sodium hydrogen carbonate and water in that order and dried over anhydrous sodium sulfate. The solvent is then distilled off, the residue is treated with ether, and crystals are collected by filtration. Yield 2.7 g; m.p. 119°-121° C., [α]D21.5 -14.4° (c=1.01, DMF), Rf1 0.29.

Workup

  1. additionis added
  2. filtrationthe precipitated DCU filtered off
  3. distillationthe solvent distilled off
  4. dissolutionthe residue dissolved in 200 ml of ethyl acetate
  5. washThe solution is washed with aqueous sodium hydrogen carbonate and water in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent is then distilled off
  8. additionthe residue is treated with ether, and crystals
  9. filtrationare collected by filtration

Sources & evidence

ORD record
ord-055a1209ba544ccfb907a4d0f8d1caf8
Source dataset
uspto-grants-1982_06
Patent number
US04337247

Reaction notes

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