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

HRID 642346Notes

Reaction equation

HRID 642346 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[C:9]2[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:19][C:8]=2[C:7]=1[OH:26])=[O:5])C.[NH2:27][CH2:28][C:29]([OH:31])=[O:30]>C[O-].[Na+].CO>[O:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:10]1[C:9]2[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:19][C:8]=2[C:7]([OH:26])=[C:6]([C:4]([NH:27][CH2:28][C:29]([OH:31])=[O:30])=[O:5])[N:11]=1

Participants

4

Reactant 2

HCID 750GlycineHCID 684287754-Furan-2-yl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 24757330[(4-Furan-2-yl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 53%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-furan-2-yl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (78 mg, 0.21 mmole) and glycine (320 mg, 4.26 mmole) in 0.5 M sodium methoxide/methanol (8.1 ml) was refluxed for 4 days before it was cooled to room temperature and concentrated in vacuo. Water (100 ml) and 0.1 N HCl (2.5 ml) were added to the residue and the suspension was extracted with dichloromethane (3×50 ml) and methyl tert-butyl ether (1×50 ml). The resulting yellow-green aqueous solution was acidified to pH=2 with 0.1 N HCl (3.5 ml). The resulting suspension was extracted with dichloromethane, washed with brine, dried over sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (44 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.17 (t, 1H), 8.25 (m, 2H), 7.94 (m, 1H), 7.82 (m, 1H), 7.64 (m, 3H), 6.76 (m, 1H), 4.08 (d, J=6.2 Hz, 2H); MS: (+) m/z 395.94 (M+1), (−) m/z 393.94 (M−1).

Workup

  1. temperaturewas refluxed for 4 days before it
  2. concentrationconcentrated in vacuo
  3. additionWater (100 ml) and 0.1 N HCl (2.5 ml) were added to the residue
  4. extractionthe suspension was extracted with dichloromethane (3×50 ml) and methyl tert-butyl ether (1×50 ml)
  5. extractionThe resulting suspension was extracted with dichloromethane
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dba8ed747d8d4c809fc514a789ec49b0
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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