Water → 1-Amino-2-(benzyloxy)-4-methylpyridinium 2,4,6-trimethylbenzenesulphonate

HRID 1486238노트

반응식

HRID 1486238 반응식
FC(F)(F)C(O)=O.O.[C:9]1([CH3:27])[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[S:17]([O:20]/[N:21]=C(/OCC)\C)(=[O:19])=[O:18].[CH2:28]([O:35][C:36]1[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][N:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl.C(OCC)C>[CH3:16][C:11]1[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([CH3:27])[C:10]=1[S:17]([O-:20])(=[O:19])=[O:18].[NH2:21][N+:37]1[CH:38]=[CH:39][C:40]([CH3:42])=[CH:41][C:36]=1[O:35][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 6282444Ethyl O-MesitylsulfonylacetohydroxamateHCID 142234762-(Benzyloxy)-4-methylpyridine

생성물 1

HCID 1178578501-Amino-2-(benzyloxy)-4-methylpyridinium 2,4,6-trimethylbenzenesulphonate수율 47.6%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

반응 조건

온도
-5 °C

실험 절차

A mixture of 18.0 ml of trifluoroacetic acid (233 mmol, 10 eq.) and 2.66 ml of water was cooled to −5° C. At this temperature, 9.99 g (35.0 mmol, 1.5 eq.) of ethyl (1E)-N-[(mesitylsulphonyl)oxy]ethanimidoate [CAS No: 38202-27-6] were added in portions. After 1.5 h, 150 ml of ice-water were added, and the mixture was stirred briefly and extracted with 100 ml of dichloromethane. The organic phase was dried with magnesium sulphate and filtered, and the resulting solution of O-(2-mesitylenesulphonyl)hydroxylamine (MSH) was added dropwise directly to a solution, cooled to 0° C., of 4.65 g (23.3 mmol, 1.0 eq.) of 2-(benzyloxy)-4-methylpyridine from Example 5A in 50 ml of dichloromethane. The mixture was stirred at RT for 2 h. Subsequently, 1 l of diethyl ether was added dropwise, and precipitated solids were filtered off, washed with 250 ml of diethyl ether and dried. 4.6 g of the title compound were isolated (48% of theory).

후처리

  1. extractionextracted with 100 ml of dichloromethane
  2. dry with materialThe organic phase was dried with magnesium sulphate
  3. filtrationfiltered
  4. additionthe resulting solution of O-(2-mesitylenesulphonyl)hydroxylamine (MSH) was added dropwise directly to a solution
  5. stirringThe mixture was stirred at RT for 2 h
  6. customprecipitated solids
  7. filtrationwere filtered off
  8. washwashed with 250 ml of diethyl ether
  9. customdried

출처 및 근거

ORD 기록
ord-861639ceb275422697abb3179635dc0d
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422285B2

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