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

HRID 642302Notes

Reaction equation

HRID 642302 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([CH2:12][CH3:13])[C:9]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:16][C:8]=2[C:7]=1[OH:23])=[O:5])C.[NH2:24][CH2:25][C:26]([OH:28])=[O:27]>C[O-].[Na+].CO>[CH2:12]([C:10]1[C:9]2[N:14]=[C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[S:16][C:8]=2[C:7]([OH:23])=[C:6]([C:4]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:5])[N:11]=1)[CH3:13]

Participants

4

Reactant 2

HCID 750GlycineHCID 684277474-Ethyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 24757157[(4-Ethyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 82.3%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-ethyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (57 mg, 0.17 mmol) and glycine (259 mg, 3.45 mmol) in 0.5 M sodium methoxide/methanol (6.5 mL) was refluxed for 21 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (10 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (5 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (50 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.04 (br s, 1H), 9.22 (br s, 1H), 8.17 (m, 2H), 7.64 (m, 3H), 4.05 (d, J=6.2 Hz, 2H), 3.28 (q, J=7.8 Hz, 2H), 1.42 (t, J=7.8 Hz, 3H); MS: (+) m/z 357.97 (M+1), (−) m/z 355.95 (M−1).

Workup

  1. temperaturewas refluxed for 21 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (10 mL)
  4. extractionextracted twice with dichloromethane
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d183f92d11194cd0afe4c8e0f487ea09
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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