Glycine → [(4-Ethynyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid

HRID 642376Notes

Reaction equation

HRID 642376 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]#[C:13][Si](C)(C)C)[C:9]2[N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:20][C:8]=2[C:7]=1[OH:27])=[O:5])C.[NH2:28][CH2:29][C:30]([OH:32])=[O:31]>C[O-].[Na+].CO>[C:12]([C:10]1[C:9]2[N:18]=[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[S:20][C:8]=2[C:7]([OH:27])=[C:6]([C:4]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:5])[N:11]=1)#[CH:13]

Participants

4

Reactant 2

HCID 750GlycineHCID 684262687-Hydroxy-2-phenyl-4-trimethylsilanylethynyl-thiazolo[4,5-c]pyridine-6 carboxylic acid ethyl ester

Product 1

HCID 24757507[(4-Ethynyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 97%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-phenyl-4-trimethylsilanylethynyl-thiazolo[4,5-c]pyridine-6 carboxylic acid ethyl ester (113 mg, 0.28 mmole) and glycine (750 mg, 9.99 mmole) in 0.5 M sodium methoxide/methanol (20 ml) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (30 ml) and extracted with dichloromethane (2×40 ml). The remaining aqueous layer was acidified to pH=2 with 1N HCl. The suspension was extracted with ethyl acetate (2×40 ml), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (96 mg). MS: (+) m/z 354.20 (M+1), (−) m/z 352.16 (M−1).

Workup

  1. temperaturewas refluxed for 3 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (30 ml)
  4. extractionextracted with dichloromethane (2×40 ml)
  5. extractionThe suspension was extracted with ethyl acetate (2×40 ml)
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a13139201b5941018b3378f7d8256faf
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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