Glycine → HCID 24757332, compound

HRID 642352Notes

Reaction equation

HRID 642352 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[S:14][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>>[OH:23][C:7]1[C:8]2[S:14][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])=[N:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:5]

Participants

4

Reactant 3

HCID 750GlycineHCID 23694274Sodium methanolate methanolHCID 68426275HCID 68426275, compound

Product 1

HCID 24757332HCID 24757332, compoundYield 72.7%

Procedure

A mixture of 7-hydroxy-2-(2-methoxy-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (120 mg, 0.36 mmole) and glycine (546 mg, 7.27 mmole) in 0.5 M sodium methoxide/methanol (13.8 ml, 6.91 mmole) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (25 ml) and extracted with methyl tert-butyl ether (2×25 ml). The remaining aqueous layer was acidified to pH=3 with 1N HCl (9 ml). The resulting jelly was extracted with dichloromethane and ethyl acetate. The organic layer was combined, washed with brine and dried in vacuo to give the title compound as a yellow solid (94 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.39 (br s, 1H), 8.88 (s, 1H), 8.45 (d, 1H), 7.62 (m, 1H), 7.33 (d, 1H), 7.18 (t, 1H), 4.01 (s, 3H), 4.03 (d, 2H); MS: (+) m/z 360.25 (M+1).

Workup

  1. temperaturewas refluxed for 3 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (25 ml)
  4. extractionextracted with methyl tert-butyl ether (2×25 ml)
  5. extractionThe resulting jelly was extracted with dichloromethane and ethyl acetate
  6. washwashed with brine
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1fbbdc7fe1394b56b231240633d758d1
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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