Dicyclohexylcarbodiimide → HCID 22825549, compound

HRID 1388105Notes

Reaction equation

HRID 1388105 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([O:29][C:30](=[O:38])[CH2:31][CH2:32][C@H:33]([C:35](=[O:37])[NH2:36])[NH2:34])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH2:22]([O:29][C:30](=[O:38])[CH2:31][CH2:32][C@H:33]([C:35](=[O:37])[NH2:36])[NH:34][C:19](=[O:21])[C@H:9]([CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 12917486HCID 12917486, compound

Product 1

HCID 22825549HCID 22825549, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-t-butyloxycarbonyl-O-benzyl-L-serine (4.43 g, 15 m mols) and D-isoglutamine benzyl ester (3.54 g, 15 m mols) were dissolved in acetonitrile (100 ml), and under ice-cooling, N,N'-dicyclohexylcarbodiimide (3.50 g, 17 m mols) was added. The mixture was stirred under ice-cooling for 3 hours and, then, at room temperature for 15 hours. The precipitate was filtered off, the solvent was distilled off and the residue was dissolved in ethyl acetate (100 ml). The solution was washed with 1 N-hydrochloric acid, 5% aqueous sodium hydrogen carbonate and water in the order mentioned and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was crystallized from ethyl acetate-petroleum ether. By the above procedure there was obtained 3.40 g of N-t-butyloxycarbonyl-O-benzyl-L-seryl-D-isoglutamine benzyl ester. m.p. 65°-66° C.; [α]D23 +5.7° (c=0.5, ethanol); Rf1 -0.73.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling for 3 hours
  3. filtrationThe precipitate was filtered off
  4. distillationthe solvent was distilled off
  5. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  6. washThe solution was washed with 1 N-hydrochloric acid, 5% aqueous sodium hydrogen carbonate and water in the order
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-4a88f997b74a49879b75eb8f2a255fff
Source dataset
uspto-grants-1984_02
Patent number
US04430265

Reaction notes

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