Glycine → HCID 24757241, compound

HRID 642323Notes

Reaction equation

HRID 642323 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH3:15])[C:9]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:18][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>[CH2:12]([C:10]1[C:9]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:18][C:8]=2[C:7]([OH:25])=[C:6]([C:4]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:5])[N:11]=1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 750GlycineHCID 68427564HCID 68427564, compound

Product 1

HCID 24757241HCID 24757241, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-butyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (41 mg, 0.12 mmol) and glycine (175 mg, 2.32 mmol) in 0.5 M sodium methoxide/methanol (4.4 mL) was refluxed for 48 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (20 mL) and extracted twice with methyl t-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (3.5 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (19 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.19 (br s, 1H), 8.17 (m, 2H), 7.63 (m, 3H), 4.05 (d, J=5.8 Hz, 2H), 3.33 (m, 2H), 1.88 (m, 2H), 1.41 (m, 2H), 0.97 (t, J=7.2 Hz, 3H); MS: (+) m/z 386.13 (M+1), (−) m/z 384.13 (M−1).

Workup

  1. temperaturewas refluxed for 48 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (20 mL)
  4. extractionextracted twice with methyl t-butyl ether
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-2e0089ea49c6400f890cf9a96a18aa4f
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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