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Glycine → [(7-Hydroxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid

HRID 642382
Notes
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Reaction equation

HRID 642382 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S: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[S:20][C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[N:18][C:9]=2[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:11][C:6]=1[C:4]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 750GlycineHCID 684277447-Hydroxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 24757509[(7-Hydroxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acidYield 97%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 7-hydroxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (39 mg, 0.10 mmole) and glycine (573 mg, 7.63 mmole) in 0.5 M sodium methoxide/methanol (10.2 ml) was refluxed for 25 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (40 ml) and extracted three times with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (6 ml). The suspension was extracted with ethyl acetate (2×40 ml). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (40 mg). MS: (+) m/z 413.30 (M+1), MS: (−) m/z 411.33 (M−1).

Workup

  1. temperaturewas refluxed for 25 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (40 ml)
  4. extractionextracted three times with dichloromethane
  5. extractionThe suspension was extracted with ethyl acetate (2×40 ml)
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a60d549e490a4fdf951055ca1a482e38
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696223B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes