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

HRID 59748노트

반응식

HRID 59748 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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]+).

후처리

  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)

출처 및 근거

ORD 기록
ord-81592831319546c0b88547d4365b86a8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440954B2

반응 노트

불러오는 중…