Sodium Hydroxide → HCID 68146448, compound

HRID 1576068Notes

Reaction equation

HRID 1576068 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[C:12]([NH2:13])=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][S:9]1.[OH-].[Na+]>CO>[NH2:13][C:12]1[CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:18])=[O:2])[S:9][CH2:10][C:11]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68147790HCID 68147790, compound

Product 1

HCID 68146448HCID 68146448, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 27.3 g (.1 mole) of 3-amino-4-carbomethoxy-2,5-dihydro-2-thiophenevaleric acid methyl ester in 250 ml dry methanol was added 4.0 g (0.1 mole) of sodium hydroxide pellets. The reaction mixture was refluxed 4.0 hrs, cooled and concentrated to a volume of 50 ml. The residue was taken up in 80 ml dichloromethane and transfered to a separatory funnel. After the addition of 150 ml of 10% by weight aqueous sodium bicarbonate solution, the aqueous layer was extracted twice with 50 ml portions of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and evaporated to yield 6.4 g (0.0234 mole) of recovered starting material. The aqueous phase was adjusted to pH 1 with 6 N hydrochloric acid and extracted three times with 75 ml portions of dichloromethane. The organic phases were pooled, dried over anhydrous sodium sulfate, and evaporated to yield 18.3 g (0.071 mole, 71%) of 3-amino- 4-carbomethoxy-2,5-dihydro-2-thiophenevaleric acid as a tan solid, upon trituration with pet. ether.

Workup

  1. temperatureThe reaction mixture was refluxed 4.0 hrs
  2. temperaturecooled
  3. concentrationconcentrated to a volume of 50 ml
  4. customtransfered to a separatory funnel
  5. additionAfter the addition of 150 ml of 10% by weight aqueous sodium bicarbonate solution
  6. extractionthe aqueous layer was extracted twice with 50 ml portions of dichloromethane
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customto yield 6.4 g (0.0234 mole)
  10. customof recovered
  11. extractionextracted three times with 75 ml portions of dichloromethane
  12. dry with materialdried over anhydrous sodium sulfate
  13. customevaporated

Sources & evidence

ORD record
ord-970ab7e88c7a4be1a9c666d153d63f72
Source dataset
uspto-grants-1976_09
Patent number
US03979396

Reaction notes

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