Diisopropylethylamine → HCID 60637030, compound

HRID 275288Notes

Reaction equation

HRID 275288 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].C(N(CC)C(C)C)(C)C.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24](Cl)=[O:25].OS([O-])(=O)=O.[K+]>CN(C)C=O.C(OCC)(=O)C>[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])=[O:25]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 516920Potassium bisulfateHCID 2734767Methyl 3-aminopropanoate hydrochloride

Product 1

HCID 60637030HCID 60637030, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To an ice-bath-cooled solution of 0.45 g (3.2 mmol) of methyl β-alaninate hydrochloride and 1.14 mL of N,N-diisopropylethylamine (DIEA) in 10 mL of dimethylformamide (DMF) was added dropwise a 2 mL DMF solution of 0.51 g (3.2 mmol) of 2-thiopheneacetyl chloride. After 16 hours of stirring at room temperature, the reaction mixture was added to 50 mL of ethyl acetate (EtOAc) and 50 mL of 1M KHSO4, and the resulting layers were separated. The organic layer was washed with 2×50 mL of 1M KHSO4, 2×50 mL of a saturated KHCO3 solution, and 2×50 mL of H2O. The organic layer was then dried over Na2SO4 (anhydrous), filtered, and then concentrated under reduced pressure.

Workup

  1. customthe resulting layers were separated
  2. washThe organic layer was washed with 2×50 mL of 1M KHSO4, 2×50 mL of a saturated KHCO3 solution, and 2×50 mL of H2O
  3. dry with materialThe organic layer was then dried over Na2SO4 (anhydrous)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe0cb3291ff84a349c36b34078dc4522
Source dataset
uspto-grants-1995_02
Patent number
US05393747

Reaction notes

Loading…