Methyl Isocyanate → 1-[3-Cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-3-methyl-urea

HRID 1860145Notes

Reaction equation

HRID 1860145 reaction equation
[CH:1]1([CH2:6][C@H:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][N:20]=[C:21]=[O:22]>C1(C)C=CC=CC=1>[CH:1]1([CH2:6][C@H:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH:10][C:21]([NH:20][CH3:19])=[O:22])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 462222313-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide

Product 1

HCID 120444601-[3-Cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-3-methyl-ureaYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide (54 mg, 0,19 mmol) in toluene (5 mL) was treated with methyl isocyanate (0.03 mL, 0.47 mmol). The resulting solution was heated under reflux for 24 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh 70/30 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-3-methyl-urea (40 mg, 63%) as a white solid: mp 124.8-127.5° C.; [α]23589=−21.2° (c=0.099, chloroform); EI-HRMS m/e calcd for C16H20Cl2N2O2 (M+) 342.0902, found 342.0902.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 24 h
  3. concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-7746632ba5ea4657beeca392eabdca2f
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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