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

HRID 642340Notes

Reaction equation

HRID 642340 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([CH2:12][CH:13]([CH3:15])[CH3:14])[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>[OH:25][C:7]1[C:8]2[S:18][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:16][C:9]=2[C:10]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:11][C:6]=1[C:4]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 684281637-Hydroxy-4-isobutyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 24757247[(7-Hydroxy-4-isobutyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 77.8%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-4-isobutyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (35 mg, 0.10 mmole) and glycine (146 mg, 1.95 mmole) in 0.5 M sodium methoxide/methanol (3.7 ml) was refluxed for 4 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (12 ml) and extracted three times with methyl t-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (2.5 ml). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (30 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.18 (br s, 1H), 8.15 (m, 2H), 7.62 (m, 3H), 4.02 (d, J=5.9 Hz, 2H), 3.12 (d, 2H, J=7.4 Hz), 2.41 (m, 1H), 0.93 (d, 2H, J=6.6 Hz); MS: (+) m/z 385.98 (M+1); (−) m/z 383.99 (M−1)

Workup

  1. temperaturewas refluxed for 4 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (12 ml)
  4. extractionextracted three times with methyl t-butyl ether
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-342faf33e8384f1f90d8ece578f28cd7
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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