Dicyclohexylcarbodiimide → HCID 12802623, compound

HRID 1156947Notes

Reaction equation

HRID 1156947 reaction equation
[NH:1]([C:22]([O:24]CC1C=CC=CC=1)=O)[CH2:2][C:3]([N:5]([CH3:21])[C@H:6]([C:14]([NH:16][NH:17][C:18]([NH2:20])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH:32]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C@@H:33](C(O)=O)[CH2:34][CH2:35][C:36](=[O:38])[NH2:37].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CO.CN(C=O)C>[NH:32]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C@@H:33]([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])=[O:19])=[O:15])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4])=[O:24])[CH2:34][CH2:35][C:36](=[O:38])[NH2:37]

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 12802621HCID 12802621, compound

Product 1

HCID 12802623HCID 12802623, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

0.85 g of Z-Gly-MePhe-NHNHCONH2 is subjected to catalytic reduction in methanol, dissolved in 10 ml of DMF, and after ice-cooling, 0.50 g of BOC-(D)-Gln-OH, 0.40 g of HONB and 0.45 g of DCC are added. The mixture is stirred for 15 hours, the precipitated DCU filtered off and the solvent distilled off. The residue is dissolved in n-butanol, 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, treated with ether and filtered to obtain a powder. Yield 0.82 g; m.p. 124°-128° C.; [α]D24 -36.5° (c=1.0, DMF); Rf1 0.11.

Workup

  1. temperatureafter ice-cooling
  2. filtrationthe precipitated DCU filtered off
  3. distillationthe solvent distilled off
  4. dissolutionThe residue is dissolved in n-butanol
  5. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and water in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent is distilled off
  8. additiontreated with ether
  9. filtrationfiltered
  10. customto obtain a powder

Sources & evidence

ORD record
ord-400669816db4415dabfad9adf9a25530
Source dataset
uspto-grants-1982_06
Patent number
US04337247

Reaction notes

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