Potassium Carbonate → HCID 59485608, compound

HRID 1972256Notes

Reaction equation

HRID 1972256 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+].F[C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[C:30]#[N:31]>CS(C)=O>[C:30]([C:29]1[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=1[O:19][C:15]1[CH:14]=[C:13]([C@H:12]2[CH2:11][O:10][C:9](=[O:20])[N:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:18]=[CH:17][CH:16]=1)#[N:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 678552-FluorobenzonitrileHCID 59485707HCID 59485707, compound

Product 1

HCID 59485608HCID 59485608, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To (S)-3-(4-chlorophenyl)-4-(3-hydroxyphenyl)oxazolidin-2-one (0.07 mmol) is added K2CO3 (0.14 mmol) and 2-fluorobenzonitrile (0.08 mmol) in DMSO (1 mL). The mixture is degassed with N2 (2×) and stirred at 80° C. for 2-3 hours. The mixture is filtered through a Whatman 0.42 μM filter and purified by preparatory LC-MS (C-18, 10-90% ACN/water (0.05% TFA)). HPLC-MS calculated for C22H15ClN2O3 (M+H+): 391.1, found 391.0.

Workup

  1. customThe mixture is degassed with N2 (2×)
  2. filtrationThe mixture is filtered through a Whatman 0.42 μM
  3. filtrationfilter
  4. custompurified by preparatory LC-MS (C-18, 10-90% ACN/water (0.05% TFA))

Sources & evidence

ORD record
ord-749a3c0ce96a4a45815505101e8bd476
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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