Methanol → HCID 12044474, compound

HRID 1860211Notes

Reaction equation

C(O[C:4](=[O:25])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:21][CH2:22][CH2:23][CH3:24])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.CO.[CH3:28][NH:29][C:30]([NH2:32])=[O:31]>C[O-].[Mg+2].C[O-]>[CH2:21]([S:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[C:4]([NH:32][C:30]([NH:29][CH3:28])=[O:31])=[O:25])=[CH:17][CH:16]=1)(=[O:19])=[O:20])[CH2:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 2-[4-(butane-1-sulfonyl)-phenyl]-3-cyclopentyl-propionic acid ethyl ester (125.3 mg, 0.34 mmol) in magnesium methoxide in methanol (7.4 wt %, 0.98 mL, 0.68 mmol) was treated with methyl urea (38 mg, 0.51 mmol). This mixture was refluxed at 110° C. for 12 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 1-{2-[4-(butane-1-sulfonyl)-phenyl]-3-cyclopentyl-propionyl}-3-methyl-urea (61.8 mg, 45.8%) as a white solid: mp 189-191° C.; EI-HRMS m/e calcd for C20H30N2O4S (M+) 395.2005, found 395.2008.

Workup

concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record: ord-e367feeb1a0347818674e656f26591e9
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528543B1

Reaction notes

Loading…