Iodoethane → HCID 59485784, compound

HRID 1972258Notes

Reaction equation

HRID 1972258 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[CH2:11][O:10][C:9]2=[O:20])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:28][CH3:29]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:28][CH3:29])[CH:14]=3)[CH2:11][O:10][C:9]2=[O:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 59485707HCID 59485707, compound

Product 1

HCID 59485784HCID 59485784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To (S)-3-(4-chlorophenyl)-4-(3-hydroxyphenyl)oxazolidin-2-one (0.07 mmol), K2CO3 (0.37 mmol) in DMF (0.5 mL) is added iodoethane (0.14 mmol) and the reaction stirred at 60° C. overnight, then cooled to room temperature, filtered through a Whatman 0.42 μM filter and purified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA)). HPLC-MS calculated for C17H16ClNO3 (M+H+): 318.1, found 318.0.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a Whatman 0.42 μM
  3. filtrationfilter
  4. custompurified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA))

Sources & evidence

ORD record
ord-65f5edf41f7f45bd9492193efb08d0ad
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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