Ammonium Hydroxide → HCID 18626654, compound

HRID 1860171Notes

Reaction equation

HRID 1860171 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH: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.[OH-].[NH4+:29]>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([NH2:29])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 120676542-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid

Product 1

HCID 18626654HCID 18626654, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (147 mg, 0.44 mmol) in toluene (5 mL) with N,N-dimethylformamide (2 drops) at 25° C. was treated with oxalyl chloride (0.05 mL, 0.53 mmol). The reaction was stirred at 25° C. for 30 min. At this time, the reaction was cooled to −60° C. and treated with ammonium hydroxide (0.50 mL, 3.8 mmol). The resulting suspension was allowed to warm to 25° C. and stirred at 25° C. for 1 h. At this time, the reaction was quenched by the addition of a 2N aqueous hydrochloric acid solution (1 mL) and then extracted with diethyl ether (3×25 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 65/35 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (130 mg, 89%) as a white foam: EI-HRMS m/e calcd for C5H20ClNO3S (M+) 329.0852, found 329.0852.

Workup

  1. temperatureAt this time, the reaction was cooled to −60° C.
  2. temperatureto warm to 25° C.
  3. stirringstirred at 25° C. for 1 h
  4. customAt this time, the reaction was quenched by the addition of a 2N aqueous hydrochloric acid solution (1 mL)
  5. extractionextracted with diethyl ether (3×25 mL)
  6. dry with materialThe organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e11237a03b743c6aefadc52145e3ec5
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

Loading…