Dicyclohexylcarbodiimide → HCID 19882545, compound

HRID 1534035Notes

Reaction equation

HRID 1534035 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH:5]1[C:14]2[C:9](=[C:10]([O:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.O.OC1C2N=NNC=2C=CC=1.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][C:34]([OH:36])=O.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH2:8][CH2:7][CH2:6][CH:5]2[CH2:4][N:3]([CH3:2])[C:34](=[O:36])[CH2:33][C:29]1[S:28][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 159702-Thiopheneacetic acidHCID 23126375HCID 23126375, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 19882545HCID 19882545, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 17 (1.04 g), hydroxybenzotriazole hydrate (1.51 g) and thiopheneacetic acid (720mg) in dry THF (30 ml) at 0° C. was treated with dicyclohexylcarbodiimide (1.16 g). The reaction was warmed to room temperature and stirred for 18 hr. The mixture was filtered and concentrated. The residue was dissolved into EtOAc (60 ml) washed with 5% aq. HCl (15 ml), water (15 ml), 10% aq. KOH (15 ml), dried (MgSPO4) filtered and concentrated. Chromatography on SiO2 afforded 1.58 g of product as a viscous oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved into EtOAc (60 ml)
  4. washwashed with 5% aq. HCl (15 ml), water (15 ml), 10% aq. KOH (15 ml)
  5. dry with materialdried (MgSPO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a3e3156ded7e4cd6bf1f732ccac597be
Source dataset
uspto-grants-1992_02
Patent number
US05086074

Reaction notes

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