Glycine → HCID 11847514, compound

HRID 1465925Notes

Reaction equation

HRID 1465925 reaction equation
C(O[C:6]([C:8]1[C:9]([OH:25])=[C:10]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[S:14][C:11]2=[CH:12][N:13]=1)=[O:7])CCC.[NH2:26][CH2:27][C:28]([OH:30])=[O:29]>C[O-].[Na+].CO.Cl>[OH:25][C:9]1[C:8]([C:6]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:7])=[N:13][CH:12]=[C:11]2[S:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:16][C:10]=12

Participants

6

Reactant 2

HCID 750GlycineHCID 67234035HCID 67234035, compound

Product 1

HCID 11847514HCID 11847514, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

4-Hydroxy-2-(4-methoxy-phenyl)-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester, example 3-d, (23 mg, 0.064 mmol) and glycine (63 mg, 0.64 mmol) were suspended in 1.3 mL of 0.5 N NaOMe in methanol. The reaction mixture was heated at reflux temperature for 16 hours, cooled, and diluted with 1 N HCl to precipitate out a white solid. The precipitate was collected on a fine glass fritted filter, washed twice with water, and dried under hi-vacuum to isolate 20 mg of the title compound. MS: (+) m/z 359.04 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 16 hours
  3. temperaturecooled
  4. customto precipitate out a white solid
  5. customThe precipitate was collected on a fine glass fritted filter
  6. washwashed twice with water
  7. customdried under hi-vacuum

Sources & evidence

ORD record
ord-1ca3933cbd2a4d84bc69ac569db0732e
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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