Methanol → HCID 59761148, compound

HRID 600560Notes

Reaction equation

HRID 600560 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]([C:5]1[N:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]3[CH2:27][CH2:26][N:25]([CH3:28])[C:24]3=[O:29])[CH:21]=2)[C:15]([O:17]C)=[O:16])=[N:9][CH:10]=1)=[O:4].CO.[OH-].[Li+].O>C1COCC1>[CH3:1][N:2]([CH3:30])[C:3]([C:5]1[N:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]3[CH2:27][CH2:26][N:25]([CH3:28])[C:24]3=[O:29])[CH:21]=2)[C:15]([OH:17])=[O:16])=[N:9][CH:10]=1)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 59761156methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate2×

Product 1

HCID 59761148HCID 59761148, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 46) (772 mg, 1.86 mmol) was dissolved in THF (9 mL) and methanol (3 mL) and lithium hydroxide solution (1N, 2.2 mL) was added followed by water (25 mL). The resulting mixture was stirred for 1 hour at room temperature. The majority of the organic solvent was removed by distillation under reduced pressure. The remaining aqueous solution was extracted with ethyl acetate (10 mL) then acidified with 2N citric acid and re-extracted with ethyl acetate (5×25 mL), the combined organic extracts were washed with water (10 mL) and brine (20 mL), dried (MgSO4) and evaporated to afford the product (716 mg, 96%). 1H NMR δ (300 MHz, CDCl3) 2.13-2.27 (m, 1H), 2.55-2.69 (m, 1H), 2.96 (s, 3H), 3.17 (d, 6H), 3.35-3.58 (m, 2H), 4.98 (t, 1H), 7.10 (s, 1H), 7.45 (s, 1H), 7.63 (s, 1H), 8.36 (s, 1H), 8.53 (s, 1H); m/z 401 (M+H+).

Workup

  1. customThe majority of the organic solvent was removed by distillation under reduced pressure
  2. extractionThe remaining aqueous solution was extracted with ethyl acetate (10 mL)
  3. extractionre-extracted with ethyl acetate (5×25 mL)
  4. washthe combined organic extracts were washed with water (10 mL) and brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-314f067f464e457db53d9fc2c2ba1a6a
Source dataset
uspto-grants-2011_03
Patent number
US07902200B2

Reaction notes

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