Urea → HCID 9912134, compound

HRID 1532149Notes

Reaction equation

HRID 1532149 reaction equation
[CH2:1]([C:4]1[CH:26]=[C:25]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH:20]=[CH:21][CH:22]=1)[CH:14]([OH:19])[C:15](OC)=[O:16])[CH2:2][CH3:3].[NH2:34][C:35](N)=[O:36].C[O-].[Na+]>>[CH2:1]([C:4]1[CH:26]=[C:25]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH:14]2[O:19][C:35](=[O:36])[NH:34][C:15]2=[O:16])[CH:20]=[CH:21][CH:22]=1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 1176UreaHCID 10942334Sodium MethoxideHCID 22459050HCID 22459050, compound

Product 1

HCID 9912134HCID 9912134, compound

Procedure

A solution of methyl 3-(3-(2-propyl-4-phenoxyphenoxy)propoxy)mandelate (194 mg), urea (39 mg) and sodium methoxide (0.90 mL, 0.5 M) was refluxed overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed twice with water, dried over sodium sulfate, filtered and evaporated to an oil, which was chromatographed over silica gel with 3% of methanol in methylenechloride to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to an oil, which
  6. customwas chromatographed over silica gel with 3% of methanol in methylenechloride

Sources & evidence

ORD record
ord-f5d33262598f4a0695267d9e6c6d820e
Source dataset
uspto-grants-2001_03
Patent number
US06200998B1

Reaction notes

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