Dichloromethane → HCID 67483906, compound

HRID 1860174Notes

Reaction equation

HRID 1860174 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][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)=O.C(Cl)Cl.[OH-].[NH4+:32]>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([NH2:32])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 12067655(R)-2-(3-Chloro-4-(methylsulfonyl)phenyl)-3-cyclopentylpropanoic acid

Product 1

HCID 67483906HCID 67483906, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (200 mg, 0.61 mmol) in toluene (4.8 mL) and N,N-dimethylformamide (12 μL) at 25° C. was treated with a 2.0 M solution of oxalyl chloride in methylene chloride (0.36 mL, 0.73 mmol). This solution was stirred at 25° C. for 30 min. At this time, the reaction was cooled to −60° C. and treated dropwise with a 30% aqueous ammonium hydroxide solution (0.59 mL, 5.24 mmol). The resulting suspension was allowed to gradually warm to 25° C. and stirred at 25° C. for 1 h. The reaction mixture was then extracted with ethyl acetate (3×25 mL). The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Biotage Flash 40S column, ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (175 mg, 88%) as a colorless oil: [α]23589=−45.8° (c=0.096, chloroform); EI-HRMS m/e calcd for C15H20ClNO3S (M+) 329.0852, found 329.0851.

Workup

  1. temperatureAt this time, the reaction was cooled to −60° C.
  2. temperatureto gradually warm to 25° C.
  3. stirringstirred at 25° C. for 1 h
  4. extractionThe reaction mixture was then extracted with ethyl acetate (3×25 mL)
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1421116e4b0d4cd68995cb6fe8f47551
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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