Triethylamine → 10-(Acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane

HRID 21977

反応式

HRID 21977 の反応式
[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([CH2:19]O)[NH:11][C:10]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C1(C)C=C[C:32]([S:35]([O-])(=O)=O)=[CH:31]C=1.FC1C=CC=C[N+]=1C.S1C=CC=C1CC(O)=[O:55]>CC(C)=O.C1C=CC=CC=1>[C:32]([S:35][CH2:19][CH:12]1[NH:11][C:10](=[O:21])[CH:9]([CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:55])[CH3:31]

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 159702-Thiopheneacetic acidHCID 1716312-Fluoro-1-methylpyridinium p-toluenesulfonateHCID 199308433-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane

生成物 1

HCID 1993082910-(Acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 241Benzene溶媒

実験手順

3-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane (0.50 g, 1.67 mmol) is dissolved in acetone (5.0 mL) and benzene (5.0 mL). Triethylamine (0.26 mL, 1.9 mmol) is added, followed by 2-fluoro-1-methylpyridinium toluene-4-sulfonate (0.54 g, 1.9 mmol), and the reaction is stirred at room temperature for 90 minutes. Thiolacetic acid (0.14 mL, 1.9 mmol) and more triethylamine (0.26 mL, 1.9 mmol) are added, and the reaction is heated to reflux for 2 hours. The solvent is then removed, the crude product is partitioned between methylene chloride and water, and the aqueous phase is extracted several times with methylene chloride. The combined organic layers are dried (MgSO4) and the solvent is evaporated. The crude product is purified by silica gel chromatography (15% ethyl acetate/hexane) to give 10-(acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane, MS: M+1=358.

後処理

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent is then removed
  4. customthe crude product is partitioned between methylene chloride and water
  5. extractionthe aqueous phase is extracted several times with methylene chloride
  6. dry with materialThe combined organic layers are dried (MgSO4)
  7. customthe solvent is evaporated
  8. customThe crude product is purified by silica gel chromatography (15% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-2d71b0967d484a04a693d8513b6e2d68
出典データセット
uspto-grants-1995_06
特許番号
US05426103

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