Oxalyl chloride → 2-(3-Chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclobutyl)-propionyl chloride
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:16][CH:17]2[CH2:20][C:19](=[O:21])[CH2:18]2)[C:13](O)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(Cl)(=O)C([Cl:25])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][CH:17]2[CH2:20][C:19](=[O:21])[CH2:18]2)[C:13]([Cl:25])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclobutyl)-propionic acid (0.12 g, 0.36 mmol) in methylene chloride (10 ml) was cooled to 0° C. To this solution was added dropwise a solution of oxalyl chloride in methylene chloride (2 M solution, 0.22 ml, 0.43 mmol) and N,N-dimethylfomamide (two drops) which produced gas evolution and then it was stirred at 0° C. for 20 minutes and 40 min at 25° C. After this time, the reaction was concentrated in vacuo and azeotroped with methylene chloride (10 ml). The reaction was redissolved in methylene chloride (10 ml) to afford the crude 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(3-oxo-cyclobutyl)-propionyl chloride as a 0.012M solution which was used in the following step with no further purification.
Workup
- customproduced gas evolution
- concentrationAfter this time, the reaction was concentrated in vacuo
- customazeotroped with methylene chloride (10 ml)
- dissolutionThe reaction was redissolved in methylene chloride (10 ml)
Sources & evidence
- ORD record
- ord-a3d3ce8fc75b44f59b438fc406a33133
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935699B2
Reaction notes
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