Methanol → HCID 21282941, compound

HRID 2232886Notes

Reaction equation

HRID 2232886 reaction equation
[O:1]=[C:2]([NH:17][CH:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)[C:19]([O:21]C)=[O:20])[CH2:3][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CO>[OH-].[Na+].O1CCCC1>[O:1]=[C:2]([NH:17][CH:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)[C:19]([OH:21])=[O:20])[CH2:3][CH:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 14326879HCID 14326879, compound

Product 1

HCID 21282941HCID 21282941, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

α-[(1-Oxo-3,3-diphenylpropyl)amino]-3,4-dimethoxybenzenepropionic acid, methyl ester (6.0 g) in 1N sodium hydroxide, tetrahydrofuran, and methanol was allowed to stir at room temperature for several hours. The mixture was evaporated to 50% volume and poured into ethyl acetate and water. The layers were separated and the aqueous layer was brought to pH 2 using concentrated hydrochloric acid. The mixture was extracted with ethyl acetate (2×50 ml) and the combined extracts were washed with water, brine, dried over magnesium sulfate, filtered and evaporated at reduced pressure.

Workup

  1. customThe mixture was evaporated to 50% volume
  2. additionpoured into ethyl acetate and water
  3. customThe layers were separated
  4. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  5. washthe combined extracts were washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-b0be9e0f69a040f3b596ec7fbd9550e8
Source dataset
uspto-grants-1988_11
Patent number
US04788010

Reaction notes

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