Hydrochloric Acid → N-Cyclopropylmethyl-N-propyl-3-oxo-butanamide

HRID 1057768Notes

Reaction equation

HRID 1057768 reaction equation
[C:1]([O-:7])(=O)[CH2:2][C:3]([CH3:5])=[O:4].[Li+].C(N(CC)CC)C.[CH2:16]([NH:19][CH2:20][CH:21]1[CH2:23][CH2:22]1)[CH2:17][CH3:18].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.Cl>ClC(Cl)C>[CH:21]1([CH2:20][N:19]([CH2:16][CH2:17][CH3:18])[C:1](=[O:7])[CH2:2][C:3](=[O:4])[CH3:5])[CH2:23][CH2:22]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 117787Cyclopropanemethanamine, N-propyl-HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 27242463-oxobutanoic acid lithium salt

Product 1

HCID 18672242N-Cyclopropylmethyl-N-propyl-3-oxo-butanamideYield 49.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A stirred mixture of lithium acetoacetate (scheme 2: (G)) (1.00 g, 9.26 mmoles), triethylamine (2.58 mL, 18.5 mmoles), and n-propylcyclopropylmethyl amine (scheme 2: (E)) (1.32 mL, 9.26 mmoles) in dry dichloroethane (60 mL) was treated with bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOPCl) (2.36g, 9.26 mmoles). The mixture was stirred overnight at room temperature, and then acidified (pH˜1) with 1M hydrochloric acid. The mixture was extracted with ethyl acetate, washed with saturated sodium bicarbonate, brine, and dried over MgSO4. Concentration in vacuo and purification by silica gel chromatography (30% ethyl acetate/hexane) gave 900 mg of a yellow oil.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with saturated sodium bicarbonate, brine
  3. dry with materialdried over MgSO4
  4. concentrationConcentration
  5. customin vacuo and purification by silica gel chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5167c1d99721485caf083c33166cca75
Source dataset
uspto-grants-2003_02
Patent number
US06515005B2

Reaction notes

Loading…