Methanesulfonyl chloride → Tert-butyl 5-(methylsulfonamido)thiophene-2-carboxylate

HRID 59748ノート

反応式

HRID 59748 の反応式
NC1SC(C(OC(C)(C)C)=O)=CC=1.CS(Cl)(=O)=O.[CH3:19][S:20]([N:23]([C:28]1[S:32][C:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:30][CH:29]=1)S(C)(=O)=O)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH3:19][S:20]([NH:23][C:28]1[S:32][C:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:30][CH:29]=1)(=[O:21])=[O:22]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 86703850Tert-butyl 5-aminothiophene-2-carboxylateHCID 86703852tert-butyl 5-(N-(methylsulfonyl)-methylsulfonamido)thiophene-2-carboxylate

生成物 1

HCID 86703851Tert-butyl 5-(methylsulfonamido)thiophene-2-carboxylate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of tert-butyl 5-aminothiophene-2-carboxylate (Int. 55) (1.481 g, 7.43 mmol) in pyridine (50 ml) cooled to 0° C., methanesulfonyl chloride (0.695 ml, 8.92 mmol) was added drop-wise. The reaction was warmed to RT and stirred for 3 days. The solvent was removed under vacuum, and the residue was portioned between EtOAc and 1N HCl; the organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. The crude was purified by flash chromatography on silica gel cartridge (petroleum ether/EtOAc=8/2) to afford tert-butyl 5-(methylsulfonamido)-thiophene-2-carboxylate (Int. 56) (773 mg, 2.79 mmol, MS/ESI+299.9 [MNa]+) and tert-butyl 5-(N-(methylsulfonyl)-methylsulfonamido)thiophene-2-carboxylate (Int. 57) (420 mg, 1.182 mmol, MS/ESI+ not detectable [MH]+).

後処理

  1. customThe solvent was removed under vacuum
  2. washthe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography on silica gel cartridge (petroleum ether/EtOAc=8/2)

出典と根拠

ORDレコード
ord-81592831319546c0b88547d4365b86a8
出典データセット
uspto-grants-2016_09
特許番号
US09440954B2

反応ノート

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