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

HRID 21977

반응식

HRID 21977 반응식
[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]

참가 물질

7

반응물 4

HCID 8471Triethylamine2회HCID 159702-Thiopheneacetic acidHCID 1716312-Fluoro-1-methylpyridinium p-toluenesulfonateHCID 199308433-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 241Benzene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2d71b0967d484a04a693d8513b6e2d68
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426103

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