Dicyclohexylcarbodiimide → HCID 12802637, compound

HRID 1156949Notes

Reaction equation

HRID 1156949 reaction equation
[NH:1]([C:22]([O:24]C(C)(C)C)=O)[CH2:2][C:3]([N:5]([CH3:21])[C@H:6]([C:14]([NH:16][NH:17][C:18]([NH2:20])=[S:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH:29]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@@H:30](C(O)=O)[CH2:31][CH2:32][C:33](=[O:35])[NH2:34].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>FC(F)(F)C(O)=O.CN(C=O)C>[NH:29]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@@H:30]([C:22]([NH:1][CH2:2][C:3]([N:5]([CH3:21])[C@H:6]([C:14]([NH:16][NH:17][C:18]([NH2:20])=[S:19])=[O:15])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4])=[O:24])[CH2:31][CH2:32][C:33](=[O:35])[NH2:34]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 2724760(2R)-2-(((tert-butoxy)carbonyl)amino)-4-carbamoylbutanoic acidHCID 12802635HCID 12802635, compound

Product 1

HCID 12802637HCID 12802637, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 6422Trifluoroacetic acidSolvent

Procedure

In 10 ml of trifluoroacetic acid is dissolved 0.80 g of BOC-Gly-MePhe-NHNHCSNH2, and the solution is shaken for 10 minutes, concentrated, treated with ether and filtered to obtain a powder. This powder is dissolved in 10 ml of DMF, and after ice-cooling, the solution is neutralized with 10 ml of DMF and 0.05 g BOC-(D)-Gln-OH, 0.40 g of HONB and 0.45 g of DCC are added. The mixture is stirred for 20 hours. The precipitated DCU is filtered off, the solvent distilled off and the residue dissolved in n-butanol. The solution is washed with a saturated aqueous solution of sodium hydrogen carbonate and water in that order and dried over anhydrous sodium sulfate. The solvent is distilled off and the residue is treated with ether and filtered to obtain a powder. Yield 0.73 g; m.p. 120°-123° C.; [α]D24 -46.0° (c=1.0, DMF); Rf1 0.18.

Workup

  1. concentrationconcentrated
  2. additiontreated with ether
  3. filtrationfiltered
  4. customto obtain a powder
  5. temperatureafter ice-cooling
  6. additionare added
  7. stirringThe mixture is stirred for 20 hours
  8. filtrationThe precipitated DCU is filtered off
  9. distillationthe solvent distilled off
  10. dissolutionthe residue dissolved in n-butanol
  11. washThe solution is washed with a saturated aqueous solution of sodium hydrogen carbonate and water in that order
  12. dry with materialdried over anhydrous sodium sulfate
  13. distillationThe solvent is distilled off
  14. additionthe residue is treated with ether
  15. filtrationfiltered
  16. customto obtain a powder

Sources & evidence

ORD record
ord-6f7afbe8086e4a0f8dc3fc5ba1755125
Source dataset
uspto-grants-1982_06
Patent number
US04337247

Reaction notes

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