Glycine → HCID 24757158, compound

HRID 642306Notes

Reaction equation

HRID 642306 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:14][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[S:14][C:13]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:5]

Participants

4

Reactant 3

HCID 750GlycineHCID 23694274Sodium methanolate methanolHCID 68426549HCID 68426549, compound

Product 1

HCID 24757158HCID 24757158, compoundYield 54.6%

Procedure

A mixture of 7-hydroxy-2-phenoxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (81 mg, 0.26 mmol) and glycine (386 mg, 5.14 mmol) in 0.5 M sodium methoxide/methanol (9.8 mL, 4.88 mmol) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water and extracted with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (7.3 mL). The suspension was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated in vacuo and purified on a C18 reverse column with a gradient of 0.1% TFA in water and 0.1% TFA in acetonitrile to give the title compound as a brown solid (49 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.16 (s, 1H), 9.39 (br s, 1H), 8.60 (s, 1H), 7.55 (m, 4H), 7.42 (m, 1H), 4.01 (d, J=6.4 Hz, 2H); MS: (+) m/z 346.00 (M+1).

Workup

  1. temperaturewas refluxed for 3 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with dichloromethane
  5. extractionThe suspension was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified on a C18 reverse column with a gradient of 0.1% TFA in water and 0.1% TFA in acetonitrile

Sources & evidence

ORD record
ord-812ec982c61c4c4f86d2d667c6554b9d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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