Sodium Hydroxide → HCID 117622965, compound

HRID 57051Notes

Reaction equation

HRID 57051 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:35]#[N:36])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH:31]([CH3:33])[CH3:32])[C:17]([NH:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[C:22]([CH3:30])[CH:21]=3)=[O:18])[C:10](=[O:34])[CH:9]=2)[CH:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:35]#[N:36])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH:31]([CH3:33])[CH3:32])[C:17]([NH:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[C:22]([CH3:30])[CH:21]=3)=[O:18])[C:10](=[O:34])[CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117622539Methyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-methylbutanoyl}amino)-2-methylbenzoate

Product 1

HCID 117622965HCID 117622965, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

105 mg (207 μmol) of methyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-methylbutanoyl}amino)-2-methylbenzoate (racemate) were dissolved in 4.0 ml of methanol. 0.83 ml of a 1N sodium hydroxide solution was added and the mixture was heated to reflux for 1 h. The reaction mixture was then concentrated under reduced pressure and the residue was taken up in water and acidified with 1N aqueous hydrochloric acid. The mixture was extracted with ethyl acetate, the organic phase was dried over sodium sulphate and the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (column: Chromatorex 125 mm×30 mm, 10 μm, mobile phase: 0.1% aqueous ammonium formate solution and acetonitrile, gradient 30% acetonitrile to 70% acetonitrile). The isolated product was finally triturated with water and filtered off with suction. Yield: 15 mg (15% of theory)

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 h
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe organic phase was dried over sodium sulphate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by preparative HPLC (column: Chromatorex 125 mm×30 mm, 10 μm, mobile phase: 0.1% aqueous ammonium formate solution and acetonitrile, gradient 30% acetonitrile to 70% acetonitrile)
  8. customThe isolated product was finally triturated with water
  9. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-1725584a708f4b73a235ac3812b7de4d
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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