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

HRID 1057768ノート

反応式

HRID 1057768 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 18672242N-Cyclopropylmethyl-N-propyl-3-oxo-butanamide収率 49.3%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5167c1d99721485caf083c33166cca75
出典データセット
uspto-grants-2003_02
特許番号
US06515005B2

反応ノート

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