Dicyclohexylcarbodiimide → HCID 15029792, compound

HRID 847246Notes

Reaction equation

HRID 847246 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]([OH:25])=O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:16][O:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[CH:5]([CH2:4][N:3]([CH3:2])[C:23](=[O:25])[CH2:22][C:18]1[S:17][CH:21]=[CH:20][CH:19]=1)[CH2:6][CH2:7][CH2:8]2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 159702-Thiopheneacetic acidHCID 757711-HydroxybenzotriazoleHCID 19882603HCID 19882603, compound

Product 1

HCID 15029792HCID 15029792, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 3 was converted to the free base (6 g) and dissolved in dry tetrahydrofuran (THF) (125 ml). Then 2-thiopheneacetic acid (3.62 g) and 1-hydroxybenzotriazole (5.1 g) was added followed by the dropwise addition of N,N'-dicyclohexylcarbodiimide (DCC) 6.7 g in dry THF (50 ml). The reaction was stirred at room temperature overnight, then filtered and evaporated to dryness. The oil was dissolved in EtOAc and upon standing precipitation occurred. This was filtered, and the filtrate washed with 1 N NaOH, then 1 N HCl and brine. The organic phase was dried (MgSO4), filtered and concentrated to afford the product, 7.4 g, 91% yield.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. dissolutionThe oil was dissolved in EtOAc
  4. customprecipitation
  5. filtrationThis was filtered
  6. washthe filtrate washed with 1 N NaOH
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford the product, 7.4 g, 91% yield

Sources & evidence

ORD record
ord-5c8cf54f26264a878d6078e5b822a413
Source dataset
uspto-grants-1992_08
Patent number
US05140040

Reaction notes

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