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

HRID 1057768노트

반응식

HRID 1057768 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5167c1d99721485caf083c33166cca75
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515005B2

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