Diisopropylethylamine → HCID 60637030, compound

HRID 1646885Notes

Reaction equation

HRID 1646885 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 (DlEA) 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 1 M KHSO4, and the resulting layers were separated. The organic layer was washed with 2×50 mL of 1 M 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 1 M 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-824fdf6cf53d4313bdb5bac1ab6a5886
Source dataset
uspto-grants-1993_01
Patent number
US05182272

Reaction notes

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