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

HRID 642355Notes

Reaction equation

HRID 642355 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([CH3:12])[C:9]2[S:13][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:15][C:8]=2[C:7]=1[OH:22])=[O:5])C.[NH2:23][CH2:24][C:25]([OH:27])=[O:26]>C[O-].[Na+].CO>[OH:22][C:7]1[C:8]2[N:15]=[C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[S:13][C:9]=2[C:10]([CH3:12])=[N:11][C:6]=1[C:4]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 684262337-Hydroxy-4-methyl-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 24757333[(7-Hydroxy-4-methyl-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acidYield 22.1%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-4-methyl-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (105 mg, 0.33 mmole) and glycine (500 mg, 6.65 mmole) in 0.5 M sodium methoxide/methanol (12.6 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 twice with methyl t-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (9 ml). The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (25 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.08 (br s, 1H), 9.22 (t, 1H), 8.13 (m, 2H), 7.61 (m, 3H), 4.02 (d, J=6.2 Hz, 2H), 2.72 (s, 3H); MS: (+) m/z 344.26 (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 twice with methyl t-butyl ether
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1e7a9378ca4a4b7a8f99901a97933dc9
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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