海萝胶 → Methyl 3-[[(1,1-dimethylethyl)amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate

HRID 1081235

反应方程式

HRID 1081235 反应方程式
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.Cl[C:21]([O:23][CH3:24])=[O:22].Cl>C1COCC1.[Au]>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:21]([O:23][CH3:24])=[O:22])(=[O:8])=[O:7])([CH3:1])[CH3:3]

参与物

7

反应物 4

HCID 313海萝胶HCID 6586氯甲酸甲酯HCID 19693811N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamideHCID 178418339正丁基锂

产物 1

HCID 19693837Methyl 3-[[(1,1-dimethylethyl)amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate收率 55.9%

试剂、催化剂与溶剂 2

HCID 23985Gold催化剂2 次HCID 8028四氢呋喃溶剂

反应条件

温度
-78 °C

实验过程

To a solution of 5 g (23 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -65° C., 20 mL (47.4 mmol) 2.32M n-butyllithium in hexanes. The resulting amber turbid solution was stirred at -78° C. for ca. 30 minutes. 1.87 mL (24.3 mmol) of methyl chloroformate was add in one portion and the resulting gold reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The gold reaction mixture was cooled to 0° C. and acidified with 1N HCl. The THF phase was separated, washed with brine, dried (MgSO4) and concentrated to an amber oil. The oil was combined with the crude product from the previous example and chromatographed on silica (30% ethyl acetate/70% hexanes) affording 3.53 g of the title compound as a solid.

后处理

  1. additionwas added dropwise
  2. temperatureto warm to room temperature
  3. stirringstir for ca. 1.5 hours
  4. temperaturewas cooled to 0° C.
  5. customThe THF phase was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated to an amber oil
  9. customchromatographed on silica (30% ethyl acetate/70% hexanes)

来源与证据

ORD记录
ord-de6c797c069e46d4b339ae61bc0bbbb9
来源数据集
uspto-grants-1996_12
专利号
US05585328

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