Glycine → HCID 11846030, compound

HRID 2368752Notes

Reaction equation

HRID 2368752 reaction equation
C(O[C:6]([C:8]1[C:9]([OH:23])=[C:10]2[CH:22]=[CH:21][S:20][C:11]2=[C:12]([C:14]#[C:15][Si](C)(C)C)[N:13]=1)=[O:7])CCC.C[O-].[Na+].CO.[NH2:29][CH2:30][C:31]([OH:33])=[O:32]>>[C:14]([C:12]1[N:13]=[C:8]([C:6]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:7])[C:9]([OH:23])=[C:10]2[CH:22]=[CH:21][S:20][C:11]=12)#[CH:15]

Participants

5

Reactant 4

HCID 750GlycineHCID 887MethanolHCID 10942334Sodium MethoxideHCID 67233834HCID 67233834, compound

Product 1

HCID 11846030HCID 11846030, compoundYield 101.4%

Procedure

A mixture of 4-hydroxy-7-trimethylsilanylethynyl-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (70 mg, 0.2 mmol) and a 0.5 M solution of sodium methoxide in methanol (10 ml, 5 mmol) was refluxed with stirring for 1 h before glycine (375 mg, 5 mmol) was added. Refluxing and stirring was continued for 18 h before the mixture was concentrated in vacuo. The residue was dissolved in water (20 ml), and the pH of the solution was adjusted to 2-3 by addition of 6 N aqueous HCl. The resulting suspension was extracted with ethyl acetate (1×20 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a tan solid (56 mg); MS-(+)-ion: M+1=277.1.

Workup

  1. additionwas added
  2. temperatureRefluxing
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe residue was dissolved in water (20 ml)
  5. additionthe pH of the solution was adjusted to 2-3 by addition of 6 N aqueous HCl
  6. extractionThe resulting suspension was extracted with ethyl acetate (1×20 ml)
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8d7ebc80c9f4de091ea74fef35e1e4b
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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