Oxalyl chloride → 3-cyclopentyl-2(R)-(3-trifluoromethyl-phenyl)-propionyl chloride

HRID 546143Notes

Reaction equation

HRID 546143 reaction equation
[CH:1]1([CH2:6][C@H:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:24])=O>C(Cl)Cl>[CH:1]1([CH2:6][C@H:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:8]([Cl:24])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 671901373-cyclopentyl-2(R)-(3-trifluoromethyl-phenyl)-propionic acid

Product 1

HCID 866180483-cyclopentyl-2(R)-(3-trifluoromethyl-phenyl)-propionyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-cyclopentyl-2(R)-(3-trifluoromethyl-phenyl)-propionic acid (prepared as in Example 79, 210 mg, 0.73 mmol) was dissolved in methylene chloride (10 mL) and N,N-dimethylfomamide (one drop) and cooled to 0° C. To this solution was added dropwise a solution of oxalyl chloride in methylene chloride (2 M solution, 421 μL, 0.84 mmol) which produced gas evolution and it was then warmed to 25° C. and stirred for 1 h. After this time, the reaction was concentrated in vacuo to about 1.5 mL and then enough methylene chloride was added to bring the total volume to 6 mL. This resulted in a roughly 0.12 M solution of 3-cyclopentyl-2(R)-(3-trifluoromethyl-phenyl)-propionyl chloride which was used crude without purification.

Workup

  1. customproduced gas evolution and it
  2. temperaturewas then warmed to 25° C.
  3. concentrationAfter this time, the reaction was concentrated in vacuo to about 1.5 mL
  4. additionenough methylene chloride was added

Sources & evidence

ORD record
ord-61828247b635454897821452335b5fde
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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