Dicyclohexylcarbodiimide → HCID 19882545, compound

HRID 847250Notes

Reaction equation

HRID 847250 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.ON1C2C=CC=CC=2N=N1.[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 27960291-Hydroxybenzotriazole hydrateHCID 23126375HCID 23126375, compound

Product 1

HCID 19882545HCID 19882545, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 17 (1.04 g), 1-hydroxybenzotriazole hydrate (1.51 g) and 2-thiopheneacetic acid (720 mg) 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 (MgSO4) 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 (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-33053962bd9e4060953f2dbad00fee15
Source dataset
uspto-grants-1992_08
Patent number
US05140040

Reaction notes

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