Glycine → HCID 68426717, compound

HRID 642560Notes

Reaction equation

HRID 642560 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[S:14][C:8]=2[C:7]=1[OH:19])=[O:5])C.[NH2:20][CH2:21][C:22]([OH:24])=[O:23]>C[O-].[Na+].CO>[C:15]([C:13]1[S:14][C:8]2[C:7]([OH:19])=[C:6]([C:4]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:5])[N:11]=[CH:10][C:9]=2[N:12]=1)([CH3:16])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 750GlycineHCID 68426440HCID 68426440, compound

Product 1

HCID 68426717HCID 68426717, compoundYield 8.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 2-tert-butyl-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (103 mg, 0.37 mmol) and glycine (247 mg, 3.3 mmol) in 5.9 mL of 0.5 N NaOMe in methanol was heated to 120° C. for 15 min with microwave irradiation using a CEM Discovery microwave reactor. The resultant mixture was concentrated under reduced pressure and the residue was suspended in ethyl acetate and extracted three times with saturated aqueous sodium bicarbonate solution. The combined aqueous fractions were acidified with conc. HCl and extracted twice with ethyl acetate. The organic fractions were dried over anhydrous sodium sulfate and concentrated to a residue. The crude product was purified by reverse phase chromatography on a C-18 column, eluting the desired product with a gradient of 5-80% acetonitrile in water+0.1% formic acid. The lyophilized material fractions provided 10 mg of white solid. MS (ESI−): m/z 308.1 (M−1).

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. extractionextracted three times with saturated aqueous sodium bicarbonate solution
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic fractions were dried over anhydrous sodium sulfate
  5. concentrationconcentrated to a residue
  6. customThe crude product was purified by reverse phase chromatography on a C-18 column
  7. washeluting the desired product with a gradient of 5-80% acetonitrile in water+0.1% formic acid

Sources & evidence

ORD record
ord-b3c243226e9b4de883c82deaaffb17f5
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

Loading…