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

HRID 642359Notes

Reaction equation

HRID 642359 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[S:18][C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:20][C:8]=2[C:7]=1[OH:27])=[O:5])C.[NH2:28][CH2:29][C:30]([OH:32])=[O:31]>C[O-].[Na+].CO>[OH:27][C:7]1[C:8]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[S:18][C:9]=2[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:11][C:6]=1[C:4]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:5]

Participants

4

Reactant 2

HCID 750GlycineHCID 684262907-Hydroxy-2,4-diphenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 24757334[(7-Hydroxy-2,4-diphenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2,4-diphenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (93 mg, 0.25 mmole) and glycine (372 mg, 4.95 mmole) in 0.5 M sodium methoxide/methanol (9.4 ml) was refluxed for 4 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (50 ml) and extracted twice with methyl t-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (7 ml). The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (79 mg). 1H NMR (DMSO-d6, 200 MHz): δ=13.28 (br s, 1H), 9.42 (t, 1H, J=6.2 Hz), 8.16 (m, 4H), 7.62 (m, 6H), 4.07 (d, 2H, J=5.8 Hz); MS: (+) m/z 406.27 (M+1).

Workup

  1. temperaturewas refluxed for 4 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (50 ml)
  4. extractionextracted twice with methyl t-butyl ether
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-948442e540724d92849dc41493448c6c
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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