(NE,S)-2-methyl-N-(oxetan-3-ylmethylidene)propane-2-sulfinamide → (S)-2-methyl-propane-2-sulfinic acid ((R)-1-oxetan-3-yl-ethyl)-amide

HRID 246272노트

반응식

HRID 246272 반응식
[O:1]1[CH2:4][CH:3](/[CH:5]=[N:6]/[S@:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8])[CH2:2]1.[CH3:13][Mg]Br>ClCCl>[O:1]1[CH2:4][CH:3]([C@H:5]([NH:6][S@:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8])[CH3:13])[CH2:2]1

참가 물질

4

반응물 2

HCID 89421069(NE,S)-2-methyl-N-(oxetan-3-ylmethylidene)propane-2-sulfinamideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 71288452(S)-2-methyl-propane-2-sulfinic acid ((R)-1-oxetan-3-yl-ethyl)-amide수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-76 °C

실험 절차

In a round-bottomed flask, (S)-2-methyl-propane-2-sulfinic acid 1-oxetan-3-yl-meth-(E)-ylideneamide (172 mg, 0.91 mmol) was dissolved in dichloromethane (3.6 ml). The colorless solution was cooled to −76° C. and methylmagnesium bromide (3.0 M in diethyl ether, 0.91 ml, 2.73 mmol) was added dropwise. The reaction mixture was stirred at −76° C. for 3 h and then allowed to warm slowly to room temperature overnight. The reaction was quenched with saturated NH4Cl-solution then extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to provide 143 mg (77%) of (S)-2-methyl-propane-2-sulfinic acid ((R)-1-oxetan-3-yl-ethyl)-amide as a light yellow oil which was used without further purification.

후처리

  1. temperatureto warm slowly to room temperature overnight
  2. customThe reaction was quenched with saturated NH4Cl-solution
  3. extractionthen extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7638b1a6d98348559483e747048f0fe4
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

반응 노트

불러오는 중…