Urea → HCID 9912134, compound

HRID 613404Notes

Reaction equation

HRID 613404 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-ca899652bbb94553b35901c5e5d79358
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

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