Glycine → HCID 11845661, compound

HRID 1465963Notes

Reaction equation

HRID 1465963 reaction equation
C(O[C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12]([Cl:14])[N:13]=1)=[O:7])CCC.[NH2:19][CH2:20][C:21]([OH:23])=[O:22].CO[Na].CO>>[Cl:14][C:12]1[N:13]=[C:8]([C:6]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:7])[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]=12

Participants

5

Reactant 4

HCID 750GlycineHCID 887MethanolHCID 86607516HCID 86607516, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 11845661HCID 11845661, compoundYield 96.3%

Procedure

A mixture of 7-chloro-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (143 mg, 0.5 mmol), glycine (751 mg, 10 mmol), and a 0.5 M solution of MeONa in methanol (20 ml, 10 mmol) was refluxed with stirring for 24 h before it was concentrated in vacuo. To the residue was added H2O (10 ml) and the pH of the mixture was adjusted to 1 to 2 by addition of 6 N HCl. The resulting suspension was extracted with EtOAc (1×25 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a tan solid (138 mg). MS-(−)-ion: M−1=285.0.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionTo the residue was added H2O (10 ml)
  3. additionthe pH of the mixture was adjusted to 1 to 2 by addition of 6 N HCl
  4. extractionThe resulting suspension was extracted with EtOAc (1×25 ml)
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7679bff8f134507a5fb95d32fbeab9f
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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