Glycine → HCID 68427327, compound

HRID 642388Notes

Reaction equation

HRID 642388 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:25])=[O:5])C.[NH2:26][CH2:27][C:28]([OH:30])=[O:29]>C[O-].[Na+].CO>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:13]2[S:14][C:8]3[C:7]([OH:25])=[C:6]([C:4]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:5])[N:11]=[CH:10][C:9]=3[N:12]=2)=[CH:16][CH:17]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 750GlycineHCID 68427838HCID 68427838, compound

Product 1

HCID 68427327HCID 68427327, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

2-(4-tert-Butyl-phenyl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (100 mg, 0.28 mmol) and glycine (442 mg, 5.89 mmol) were suspended in 11.2 mL of 0.5 N sodium methoxide in methanol. The reaction was heated at reflux temperature overnight, cooled, and concentrated. The residue was dissolved in water (30 mL), and the solution was acidified to pH 1˜2 with 2 N HCl, extracted with ethyl acetate. The combined organic layers were dried, filtered and concentrated to produce 63 mg of a yellow solid. MS: (+) m/z 386.0 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux temperature overnight
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in water (30 mL)
  6. extractionextracted with ethyl acetate
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e9cc3f1b638a4570803b9fc2a4e7142d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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