Ethyl chloroformate → HCID 11425382, compound

HRID 2083916Notes

Reaction equation

HRID 2083916 reaction equation
[O:1]=[S:2]1(=[O:12])[CH2:6][C:5]2[C:7]([OH:11])=[CH:8][CH:9]=[CH:10][C:4]=2[NH:3]1.Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15]>N1C=CC=CC=1>[CH2:17]([O:16][C:14]([N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:5]=2[CH2:6][S:2]1(=[O:12])=[O:1])=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 11183046HCID 11183046, compound

Product 1

HCID 11425382HCID 11425382, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Sultam 1c (100 mg, 0.54 mmol) was dissolved in pyridine (2.5 mL) and cooled to 0° C. Ethyl chloroformate (62 μL, 0.65 mmol) was added and the solution was warmed to room temperature and allowed to age for 16 hours. The pyridine was removed in vacuo and the reaction mixture was diluted with EtOAc, washed twice with 1.0 N HCl, once with water and once with brine. The solution was then dried over MgSO4, filtered and the solvent removed in vacuo. Purification via flash chromatography gave the desired phenol 1d (37 mg, 27%).

Workup

  1. temperaturethe solution was warmed to room temperature
  2. customThe pyridine was removed in vacuo
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed twice with 1.0 N HCl, once with water and once with brine
  5. dry with materialThe solution was then dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customPurification via flash chromatography

Sources & evidence

ORD record
ord-3581447505334935908aac4c8e9187f9
Source dataset
uspto-grants-2004_04
Patent number
US06716836B2

Reaction notes

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