Ethyl Acetate → HCID 58762326、化合物

HRID 858881ノート

反応式

HRID 858881 の反応式
[Li+].CC([N-]C(C)C)C.[CH3:9][CH2:10][O:11][C:12]([CH3:14])=[O:13].[CH:15]1([C:20](=[O:33])[CH2:21][CH2:22][NH:23][C:24](=[O:32])[CH2:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1>C1COCC1>[CH2:10]([O:11][C:12](=[O:13])[CH2:14][C:20]([CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)([OH:33])[CH2:21][CH2:22][NH:23][C:24](=[O:32])[CH2:25][CH2:26][C:27]1[O:28][CH:29]=[CH:30][CH:31]=1)[CH3:9]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 2724682Lithium diisopropylamideHCID 58762649N-(3-Cyclopentyl-3-oxo-propyl)-3-furan-2-yl-propionamide

生成物 1

HCID 58762326HCID 58762326、化合物収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

To a solution of LDA (1.0 M, 1.1 mL, 1.1 mmol) cooled to −78° C. was added EtOAc (0.1 mL, 1.1 mmol). After stirring for 30 minutes, a solution of N-(3-cyclopentyl-3-oxo-propyl)-3-furan-2-yl-propionamide (100 mg, 0.38 mmol; described in Step 2 of example H(4)) dissolved in 3 mL THF was added. The reaction was stirred for 2 hours and then allowed to warm to −40° C. The reaction was quenched with 10 mL saturated NH4Cl, and the layers were separated. The aqueous layer was extracted with 3×10 mL CH2Cl2, and the organic layers were combined. After concentrating the organic layers by rotary evaporation, the product was purified by flash chromatography (86 mg, 64% yield). MS (ESI): 350 (M−H).

後処理

  1. additionwas added
  2. stirringThe reaction was stirred for 2 hours
  3. customThe reaction was quenched with 10 mL saturated NH4Cl
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with 3×10 mL CH2Cl2
  6. concentrationAfter concentrating the organic layers
  7. customby rotary evaporation
  8. customthe product was purified by flash chromatography (86 mg, 64% yield)

出典と根拠

ORDレコード
ord-7731a4a291124764bb2ed188222358d6
出典データセット
uspto-grants-2006_12
特許番号
US07148226B2

反応ノート

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