Dicyclohexylcarbodiimide → HCID 178426809, compound

HRID 1886495Notes

Reaction equation

HRID 1886495 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:6][C:5](=[O:7])[CH2:4][CH:3]1[C:8]([OH:10])=O.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.Br.Br.[NH2:39][C@H:40]([C:47]([N:49]1[CH2:56][CH2:55][CH2:54][C@H:50]1[C:51]([NH2:53])=[O:52])=[O:48])[CH2:41][C:42]1[N:46]=[CH:45][NH:44][CH:43]=1>CN(C=O)C.C(N(CC)CC)C>[CH3:11][C:2]1([CH3:1])[CH2:6][C:5](=[O:7])[CH2:4][CH:3]1[C:8]([NH:39][C@H:40]([C:47]([N:49]1[CH2:56][CH2:55][CH2:54][C@H:50]1[C:51]([NH2:53])=[O:52])=[O:48])[CH2:41][C:42]1[N:46]=[CH:45][NH:44][CH:43]=1)=[O:10]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 216436222,2-Dimethyl-4-oxocyclopentane-1-carboxylic acidHCID 178419276HCID 178419276, compound

Product 1

HCID 178426809HCID 178426809, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

In DMF (2 ml) was dissolved 2,2 dimethyl-4-oxocyclopentanecarboxylic acid [W. H. Perkin, jun., J. F. Thorpe, J. Chem. Soc., 79, 729 (1901)] (100 mg), and HOBT (108 mg) was added to the solution, followed by addition of DCC (145 mg) under cooling at 0° C. The mixture was stirred at 5° C. over night. After addition of L-histidyl-L-prolinamide dihydrobromide (265 mg) followed by addition of triethylamine (0.134 ml), the mixture was stirred at 5° C. for 4 days. After the resultant precipitate was filtered off, the filtrate was concentrated under reduced pressure to dryness and the residue was subjected to silica gel column chromatography. The fractions eluted by chloroform:methanol:ammonia water (90:10:2) were combined and concentrated to dryness to give the title compound (140 mg) was obtained as powders.

Workup

  1. additionwas added to the solution
  2. stirringthe mixture was stirred at 5° C. for 4 days
  3. filtrationAfter the resultant precipitate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure to dryness
  5. washThe fractions eluted by chloroform:methanol:ammonia water (90:10:2)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-91266a0c68b34bc3b69449d566c1bdcf
Source dataset
uspto-grants-1992_09
Patent number
US05151497

Reaction notes

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