Oxalyl chloride → HCID 86618053, compound

HRID 546201Notes

Reaction equation

HRID 546201 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][C@H:17]2[CH2:21][CH2:20][C:19]([F:23])([F:22])[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:27])=O>C(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][C@H:17]2[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]2)[C:13]([Cl:27])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 671892282-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3,3-difluoro-cyclopentyl)-propionic acid

Product 1

HCID 86618053HCID 86618053, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3,3-difluoro-cyclopentyl)-propionic acid (240 mg, 0.65 mmol) was dissolved in methylene chloride (10 mL) and N,N-dimethylformamide (one drop) and cooled to 0° C. To this solution was added dropwise a solution of oxalyl chloride in methylene chloride (2 M solution, 376 μL, 0.75 mmol) which produced gas evolution and was stirred at 0° C. for 15 min and then warmed to 25° C. and stirred for 1 h. After this time, the reaction was concentrated in vacuo to about 2 mL and then another portion of methylene chloride (˜2 mL) was added to produce a roughly 0.16 M solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3,3-difluoro-cyclopentyl)-propionyl chloride which was used.

Workup

  1. customproduced gas evolution
  2. temperaturewarmed to 25° C.
  3. stirringstirred for 1 h
  4. concentrationAfter this time, the reaction was concentrated in vacuo to about 2 mL
  5. additionanother portion of methylene chloride (˜2 mL) was added

Sources & evidence

ORD record
ord-1d67585f15f04d35b5a17d4617740152
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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