Dicyclohexylcarbodiimide → HCID 10072480, compound

HRID 1708388Notes

Reaction equation

HRID 1708388 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.OC1C2N=NNC=2C=CC=1.[CH2:37]([N:39]([CH2:43][CH3:44])[CH2:40][CH2:41][NH2:42])[CH3:38].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.C(OCC)(=O)C>[CH2:37]([N:39]([CH2:43][CH3:44])[CH2:40][CH2:41][NH:42][C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][S:18][C:9]1[NH:10][C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1)[CH3:38]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 60993N,N-DiethylethylenediamineHCID 189587125-[(4,5-Diphenyl-1H-imidazol-2-YL)sulfanyl]pentanoic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 10072480HCID 10072480, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

5-(4,5-diphenyl-1H-imidazol-2-ylthio)-pentanoic acid (3.73 g, 10.58 retool) was dissolved in 40 mL dry dimethylformamide, and treated with solid hydroxybenzotriazole hydrate (1.77 g, 13.10 retool). Then, a 20 mL dimethylformamide solution of N,N-diethylethylenediamine (2.00 mL, 14.24 mmol) was added dropwise. The mixture was cooled to 0° C., and solid dicyclohexylcarbodiimide (2.81 g, 13.62 mmol) was added in small portions over 20 minutes. The mixture was allowed to slowly warm and stirred for 48 hours, then poured into 150 mL ethyl acetate. This mixture was washed with water (3×150 mL), and the water washings were back-extracted in sequence with ethyl acetate (150 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and evaporated to afford a pale yellow oil. The oil was separated by flash chromatography (1:4 methanol-methylene chloride) to afford N-[2-(diethylamino)ethyl]-5-(4,5-diphenyl-1H-imidazol-2-ylthio)-pentanamide (3.77 g, 8.37 mmol, 79%). 1 H NMR (300 MHz, CDCl3): 7.56-7.49 (4H, m); 7.33-7.17 (6H, m); 6.91 (1H, br s); 3.16 (2H, br d, J=6 Hz); 2.97 (2H, t, J=7 Hz); 2.68-2.49 (6H, m); 2.29 (2H, t, J=6 Hz); 2.00-1.57 (4H, m); 1.02 (6H, t, J=7 Hz).

Workup

  1. temperatureto slowly warm
  2. washThis mixture was washed with water (3×150 mL)
  3. extractionthe water washings were back-extracted in sequence with ethyl acetate (150 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto afford a pale yellow oil
  7. customThe oil was separated by flash chromatography (1:4 methanol-methylene chloride)

Sources & evidence

ORD record
ord-45ae51c41ac44d2ea477acaf2e9850a1
Source dataset
uspto-grants-1994_10
Patent number
US05358946

Reaction notes

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