Triethylamine → Ethyl 1-(4-cyclopropoxybenzamido)cyclopropanecarboxylate

HRID 2068548

反応式

HRID 2068548 の反応式
[CH:1]1([O:4][C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:21][C:22]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23]1.C(N(CC)CC)C>ClCCl.CN(C=O)C>[CH:1]1([O:4][C:5]2[CH:6]=[CH:7][C:8]([C:9]([NH:21][C:22]3([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:24][CH2:23]3)=[O:11])=[CH:12][CH:13]=2)[CH2:2][CH2:3]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 386203Ethyl 1-aminocyclopropane-1-carboxylate hydrochlorideHCID 214528644-Cyclopropoxybenzoic acid

生成物 1

HCID 67234427Ethyl 1-(4-cyclopropoxybenzamido)cyclopropanecarboxylate収率 85%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a 0° C. suspension of 4-cyclopropoxybenzoic acid (24.5 g, 137.3 mmol) in dichloromethane (350 mL) containing 2 drops of DMF, slowly add oxalyl chloride (23.8 mL, 274.7 mmol). After addition, remove the cooling bath and stir for 2 hours. Concentrate the material to dryness under reduced pressure. Dissolve the residue in dichloromethane (500 mL), and then add ethyl 1-aminocyclopropanecarboxylate hydrochloride (Indofine #04-265, 24.9 g, 150.5 mmol) and triethylamine (57.2 mL, 410.4 mmol). Stir the mixture at ambient temperature for approximately 16 hours. Wash the mixture once with 10% NaHSO4 (250 mL). Separate the organic portion and extract the aqueous portion 2× with dichloromethane (200 mL). Combine the organic, dry over sodium sulfate, filter, and concentrate under reduced pressure. Purify the crude mixture by flash chromatography (0% to 45% EtOAc/Hex) to give the title compound (33.7 g, 85%): MS (m/z): 290 (M+1).

後処理

  1. additionAfter addition
  2. customremove the cooling bath
  3. concentrationConcentrate the material to dryness under reduced pressure
  4. dissolutionDissolve the residue in dichloromethane (500 mL)
  5. stirringStir the mixture at ambient temperature for approximately 16 hours
  6. washWash the mixture once with 10% NaHSO4 (250 mL)
  7. customSeparate the organic portion
  8. extractionextract the aqueous portion 2× with dichloromethane (200 mL)
  9. dry with materialCombine the organic, dry over sodium sulfate
  10. filtrationfilter
  11. concentrationconcentrate under reduced pressure
  12. customPurify the crude mixture by flash chromatography (0% to 45% EtOAc/Hex)

出典と根拠

ORDレコード
ord-66cf8552de9a4129b5ce6d2444e291c0
出典データセット
uspto-grants-2012_10
特許番号
US08299061B2

関連ノート

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