Sodium Methoxide → HCID 66701012, compound

HRID 2075511Notes

Reaction equation

HRID 2075511 reaction equation
C(O[C:4](=[O:13])[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[SH:12])C.C[O-].[Na+].[CH3:17][O:18][C:19](=[O:28])[C:20]([NH:23][C:24](=[O:27])[CH2:25]Cl)([CH3:22])[CH3:21]>CO>[CH3:17][O:18][C:19](=[O:28])[C:20]([NH:23][C:24]([C:25]1[S:12][C:6]2[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:5]=2[C:4]=1[OH:13])=[O:27])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 16217758Ethyl 5-fluoro-2-sulfanylbenzoateHCID 43700001HCID 43700001, compound

Product 1

HCID 66701012HCID 66701012, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.00 g 5-fluoro-2-mercaptobenzoic acid ethyl ester in 10 ml methanol 0.81 g of sodium methoxide were added portionwise, followed by addition of 0.97 g 2-(2-chloro-acetylamino)-2-methyl-propionic acid methyl ester. After refluxing the reaction under argon-atmosphere for 0.5 h the resulting mixture was filtrated, 20 ml water and 1.25 ml of acetic acid were added and the precipitated product was collected by filtration, washed with water, dissolved in ethyl acetate and THF, dried over sodium sulphate, filtrated and concentrated in vacuo. The resulting crude product was crystallized from diethylether to yield 1.10 g 2-[(5-fluoro-3-hydroxy-benzo[b]thiophene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester.

Workup

  1. temperatureAfter refluxing
  2. customthe reaction under argon-atmosphere for 0.5 h the resulting mixture
  3. filtrationwas filtrated
  4. addition20 ml water and 1.25 ml of acetic acid were added
  5. filtrationthe precipitated product was collected by filtration
  6. washwashed with water
  7. dissolutiondissolved in ethyl acetate
  8. dry with materialTHF, dried over sodium sulphate
  9. filtrationfiltrated
  10. concentrationconcentrated in vacuo
  11. customThe resulting crude product was crystallized from diethylether

Sources & evidence

ORD record
ord-9c566e86c3fa4c23811516f0dccf1c35
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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