Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 1-[2-(3,4-Dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionyl]-3-methyl-urea

HRID 2214065Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH:19]2[O:23]C2CCCCO2)[C:10]([NH:12][C:13]([NH:15][CH3:16])=[O:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH:19]2[OH:23])[C:10]([NH:12][C:13]([NH:15][CH3:16])=[O:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 1-{2-(3,4-dichloro-phenyl)-3-[2-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionyl}-3-methyl-urea (45 mg, 0.10 mmol) in ethanol (1.01 mL) was treated with pyridinium p-toluenesulfonate (2.5 mg, 0.01 mmol). The reaction mixture was heated to 55° C. for 5 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 100% ethyl acetate) afforded the 1-[2-(3,4-dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionyl]-3-methyl-urea (30.4 mg, 83.4%) as a white solid: mp 62–64° C.; FAB-HRMS m/e calcd for C16H20Cl2N2O3 (M+H)+ 359.0929, found 359.0929.

Workup

concentrationAt this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-6c0c604fb03745eb9c5875d7ac94e8b0
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105671B2

Reaction notes

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