Trichloroacetyl isocyanate → HCID 23648667, compound

HRID 404885Notes

Reaction equation

HRID 404885 reaction equation
[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([CH:21]([NH2:23])[CH3:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].ClC(Cl)(Cl)[C:28]([N:30]=C=O)=[O:29]>ClCCl>[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([CH:21]([NH:23][C:28]([NH2:30])=[O:29])[CH3:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 69435781HCID 69435781, compound

Product 1

HCID 23648667HCID 23648667, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Example 17F (377 mg, 1.12 mmol) in dichloromethane (10 mL) at 0° C. was added trichloroacetyl isocyanate (145 μL, 1.22 mmol). The mixture was stirred at 0° C. for 10 minutes. The reaction was concentrated and the residue was dissolved in methanol (˜60 mL) and a small amount of Na2CO3 was added. The mixture was stirred at room temperature for 3 hours before being concentrated. The residue was dissolved in dichloromethane, which was washed with water (1×) and concentrated. The residue was purified on silica gel eluting with hexane and ethyl acetate gradient to give the desired product as a white solid (286 mg, 67%), MS (DCI): m/z 382 (M+H); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.78-7.86 (m, 2H), 6.99-7.08 (m, 4H), 6.94-6.99 (m, 2H), 6.75 (s, 1H), 6.61 (d, J=8.46 Hz, 1H), 5.59 (br s, 2H), 4.90-5.02 (m, 1H), 4.53-4.63 (m, 1H), 1.41 (d, J=6.99 Hz, 3H), 1.27 (d, J=5.88 Hz, 6H).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in methanol (˜60 mL)
  3. additiona small amount of Na2CO3 was added
  4. stirringThe mixture was stirred at room temperature for 3 hours
  5. concentrationbefore being concentrated
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwhich was washed with water (1×)
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel eluting with hexane and ethyl acetate gradient

Sources & evidence

ORD record
ord-4f2ccc65782449159807d73392a382f2
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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