Dicyclohexylcarbodiimide → HCID 178448374, compound

HRID 1282710Notes

Reaction equation

HRID 1282710 reaction equation
[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@@H:2]([C:6]([OH:8])=O)[CH2:3][CH2:4][CH3:5].[NH2:19][C@H:20]([C:25]([NH:27][C@H:28]([C:39]([N:41]1[CH2:52][CH2:51][CH2:50][C@H:42]1[C:43]([NH:45][CH2:46][C:47]([NH2:49])=[O:48])=[O:44])=[O:40])[CH2:29][CH2:30][CH2:31][NH:32][C:33](=[NH:38])[NH:34][N+:35]([O-:37])=[O:36])=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CO.CN(C)C=O>[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@@H:2]([C:6]([NH:19][C@H:20]([C:25]([NH:27][C@H:28]([C:39]([N:41]1[CH2:52][CH2:51][CH2:50][C@H:42]1[C:43]([NH:45][CH2:46][C:47]([NH2:49])=[O:48])=[O:44])=[O:40])[CH2:29][CH2:30][CH2:31][NH:32][C:33](=[NH:38])[NH:34][N+:35]([O-:37])=[O:36])=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:8])[CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 10106192Z-D-Nva-OHHCID 178446036HCID 178446036, compound

Product 1

HCID 178448374HCID 178448374, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Z-(D)-Nva-OH(380 mg), H-Leu-Arg(NO2)-Pro-Gly-NH2 (690 mg.) and HONB (300 mg.) in 5 ml. of dimethylformamide is added 340 mg. of DCC at 0°C with stirring. The mixture is stirred for 2 hours at 0°C and for additional 10 hours at room temperature. The reaction mixture is filtered to remove the formed dicyclohexyl-urea, and the filtrate is evaporated to dryness. The resulting residue is dissolved in 100 ml. of chloroform and the solution is washed with 4 % aqueous sodium bicarbonate solution and water. The washed solution is dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is then triturated with a mixture of ethylacetate (25 ml.) and ether (25 ml.) to give a white powder, which is collected by filtration and reprecipitated from ethanol-ether: yield, 1.12 g., [α]D23 -50.5°(c=1.1 in Methanol), Rf1 =0.32.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove the formed dicyclohexyl-urea
  3. customthe filtrate is evaporated to dryness
  4. dissolutionThe resulting residue is dissolved in 100 ml
  5. washof chloroform and the solution is washed with 4 % aqueous sodium bicarbonate solution and water
  6. dry with materialThe washed solution is dried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue is then triturated with a mixture of ethylacetate (25 ml.) and ether (25 ml.)
  9. customto give a white powder, which
  10. filtrationis collected by filtration
  11. customreprecipitated from ethanol-ether
  12. customyield

Sources & evidence

ORD record
ord-9ee56ef1e0924f14bdc1bc8d9d0bb8da
Source dataset
uspto-grants-1976_08
Patent number
US03972859

Reaction notes

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