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

HRID 642363Notes

Reaction equation

HRID 642363 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[S:19][C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:21][C:8]=2[C:7]=1[OH:28])=[O:5])C.[NH2:29][CH2:30][C:31]([OH:33])=[O:32]>C[O-].[Na+].CO>[CH2:12]([C:10]1[C:9]2[S:19][C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:21][C:8]=2[C:7]([OH:28])=[C:6]([C:4]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:5])[N:11]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 750GlycineHCID 684267644-Benzyl-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 24757413[(4-Benzyl-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acidYield 75.5%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-benzyl-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (48 mg, 0.12 mmole) and glycine (185 mg, 2.46 mmole) in 0.5 M sodium methoxide/methanol (4.7 ml) was refluxed for 45 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (15 ml) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (3.5 ml). The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (38 mg). 1H NMR (DMSO-d6, 200 MHz): δ=13.13 (br s, 1H), 9.34 (t, 1H, J=6.0 Hz), 8.08 (m, 2H), 7.58 (m, 3H), 7.33 (m, 5H), 4.36 (s, 2H), 4.06 (d, 2H, J=5.8 Hz); MS: (+) m/z 420.29 (M+1), MS: (−) m/z 418.29 (M−1).

Workup

  1. temperaturewas refluxed for 45 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (15 ml)
  4. extractionextracted twice with dichloromethane
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d9e532f6f3d74d1292fed659ac6b7109
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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