Methylurea → HCID 10090433, compound

HRID 2214032Notes

Reaction equation

HRID 2214032 reaction equation
CO[C:3](=[O:22])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[CH3:23][NH:24][C:25]([NH2:27])=[O:26].C[O-].[Mg+2].C[O-]>CO>[CH3:21][S:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:4]([CH2:5][CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][O:7]2)[C:3]([NH:27][C:25]([NH:24][CH3:23])=[O:26])=[O:22])=[CH:17][CH:16]=1)(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 67482160HCID 67482160, compound

Product 1

HCID 10090433HCID 10090433, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-(4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-2-yl)-propionic acid methyl ester (75 mg, 0.23 mmol), methylurea (34 mg, 0.46 mmol), and a solution of magnesium methoxide in methanol (7.4 wt. %, 0.49 mL, 0.35 mmol) and methanol (0.5 mL) was heated at 100° C. for 8 h. Over time, the reaction mixture turned cloudy in appearance. At this time, the reaction was concentrated in vacuo. The residue was dissolved in ethyl acetate (10 mL) and then filtered through a pad of silica gel. The filtrate was concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 30/70 hexanes/ethyl acetate) afforded 1-[2-(4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-2-yl)-propionyl]-3-methyl-urea (5 mg, 6%) as a colorless oil: FAB-HRMS m/e calcd for C17H24N2O5S (M+H)+ 369.1484, found 369.1495.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (10 mL)
  3. filtrationfiltered through a pad of silica gel
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-dfeb8429ed304a649f9517b65078d3ae
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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