Glycine → HCID 11844975, compound

HRID 1465927Notes

Reaction equation

HRID 1465927 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-f13613c466a84aefab11e80a77fcd9ad
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

Loading…