Methanol → HCID 20230226, compound

HRID 2290772Notes

Reaction equation

HRID 2290772 reaction equation
[C:1]([CH2:4][C:5]1[N:9]=[C:8]([CH:10]([CH3:24])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([F:23])[CH:12]=2)[O:7][N:6]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH3:30]O>>[CH3:30][O:2][C:1]([CH2:4][C:5]1[N:9]=[C:8]([CH:10]([CH3:24])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([F:23])[CH:12]=2)[O:7][N:6]=1)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 136909693-Carboxymethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

Product 1

HCID 20230226HCID 20230226, compound

Procedure

To a solution of 1.27 g of 3-carboxymethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole obtained in Example 39 in 20 ml of dry methanol was added a drop of conc. sulfuric acid. The mixture was allowed to stand at room temperature overnight and then concentrated to dryness under reduced pressure. The solution of the residue in benzene was washed successively with a sodium bicarbonate solution and water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using benzene to give 0.95 g of 3-methoxycarbonylmethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole, nD25 1.5618.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. washThe solution of the residue in benzene was washed successively with a sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-92d76f0e78164e58bd375cb1429ed4dc
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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