Glycine → HCID 11844975, compound

HRID 2368715Notes

Reaction equation

HRID 2368715 reaction equation
C(O[C:6]([C:8]1[C:9]([OH:19])=[C:10]2[CH:17]=[C:16]([CH3:18])[S:15][C:11]2=[C:12]([CH3:14])[N:13]=1)=[O:7])CCC.[NH2:20][CH2:21][C:22]([OH:24])=[O:23]>C[O-].[Na+].CO.Cl>[OH:19][C:9]1[C:8]([C:6]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:7])=[N:13][C:12]([CH3:14])=[C:11]2[S:15][C:16]([CH3:18])=[CH:17][C:10]=12

Participants

6

Reactant 2

HCID 750GlycineHCID 67234395HCID 67234395, compound

Product 1

HCID 11844975HCID 11844975, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

4-Hydroxy-2,7-dimethyl-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (30 mg, 0.11 mmol, example 5-b-A) and glycine (75 mg, 1.0 mmol) were suspended in 2.0 mL of 0.5 N NaOMe in methanol. The resultant mixture was heated to 120° C. for 10 min. using a CEM microwave reactor. The reaction mixture was cooled, and diluted with 0.25 N HCl until pH <3. The mixture was extracted two times with ethyl acetate, and the organic fractions were dried over anhydrous magnesium sulfate and concentrated to 27 mg of a pale yellow solid. MS: (−) m/z 279.01 (M−1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe mixture was extracted two times with ethyl acetate
  3. dry with materialthe organic fractions were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to 27 mg of a pale yellow solid

Sources & evidence

ORD record
ord-0d0e20d3e5584522875b6547a085803b
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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