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

HRID 813

反应方程式

HRID 813 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

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 I g (4.62 mol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under a nitrogen atmosphere cooled to -78° C. was added dropwise at such a rate as to keep the temperature below -65° C. 4.1 mL (9.48 mmol) 2.32M n-butyllithium in hexanes. The resulting amber turbid solution was stirred at -78° C. for ca. 30 minutes. Methyl chloroformate (0.37 mL, 4.86 mmol) was added in one portion and the resulting gold reaction mixture was allowed to warm to room temperature and stirred 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 ember oil. The NMR of the crude reaction product was consistent with the title compound, additionally the NMR indicated that a trace of the starting material was also present. The crude material was combined with the product from a similar reaction run on the scale described below and chromatographed to give the title compound.

后处理

  1. additionwas added dropwise at such a rate as
  2. customthe temperature below -65° C
  3. temperatureto warm to room temperature
  4. stirringstirred for ca. 1.5 hours
  5. temperaturewas cooled to 0° C.
  6. customThe THF phase was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated to an ember oil
  10. customThe NMR of the crude reaction product

来源与证据

ORD记录
ord-a32d55e896f94ee09bb5a13e0797fb99
来源数据集
uspto-grants-1998_03
专利号
US05723410

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