Water → ((2-Thienylcarbonyl)amino)acetic acid

HRID 1178074Notes

Reaction equation

HRID 1178074 reaction equation
O[Li].O.C([O:6][C:7](=[O:17])[CH2:8][NH:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)=[O:11])C.C1COCC1.O>CO>[S:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:10]([NH:9][CH2:8][C:7]([OH:17])=[O:6])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 1720748Ethyl N-(thiophene-2-carbonyl)glycinate

Product 1

HCID 679227((2-Thienylcarbonyl)amino)acetic acidYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

LiOH.H2O (110 mg, 2.63 mmol) was added to a solution of [(thiophene-2-carbonyl)-amino]-acetic acid ethyl ester (140 mg, 0.66 mmol) in a mixture of MeOH (5 mL), THF (2.5 mL) and H2O (2.5 mL). The resulting mixture was stirred for 3 hrs at room temperature. The MeOH and THF were evaporated and the resulting residue was diluted with water (2 mL), acidified with citric acid and extracted with EtOAc. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford [(thiophene-2-carbonyl)-amino]-acetic acid in 70% yield. LC-MS purity: 92%.

Workup

  1. customThe MeOH and THF were evaporated
  2. additionthe resulting residue was diluted with water (2 mL)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-019afa39c9b64df397d52169620cad22
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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