Trifluoromethanesulfonic anhydride → HCID 178500919、化合物

HRID 1063622

反応式

HRID 1063622 の反応式
[OH:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O[C@H:38]1[CH2:43][CH2:42][C@H:41]([N:44]([CH3:58])[S:45]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH2:40][CH2:39]1>C(Cl)Cl.[N+](C)([O-])=O.CCOC(C)=O.OS([O-])(=O)=O.[K+]>[CH3:7][O:6][C:4](=[O:5])[CH2:3][CH2:2][O:1][C@H:38]1[CH2:39][CH2:40][C@H:41]([N:44]([CH3:58])[S:45]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:56])([F:55])[F:57])=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH2:42][CH2:43]1

参加物

9

反応物 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 685102,6-Di-tert-butylpyridine2 回HCID 80252Propanoic acid, 3-hydroxy-, methyl esterHCID 178484845HCID 178484845、化合物

生成物 1

HCID 178500919HCID 178500919、化合物収率 95.7%

試薬・触媒・溶媒 4

HCID 6344Dichloromethane溶媒HCID 6375Nitromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 516920Potassium bisulfate溶媒

実験手順

At 0° C. to a solution of 0.62 g (5.9 mmol) of methyl beta-hydroxypropionate in 4.5 mL of CH2Cl2 was added 1.4 mL (6.4 mmol, 2.4 eq) of 2,6-di-tert-butylpyridine, followed by 1.03 mL (6.2 mmol, 2.4 eq) of trifluoromethane sulfonic acid anhydride. The solution was stirred at that temperature for 2.5 h, was concentrated, and the residue was dissolved in 5 mL of nitromethane. To this solution 1 g (2.96 mmol) of trans-N-(4-hydroxy-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide and 1.3 mL (5.9 mmol, 2.0 eq) of 2,6-di-tert-butylpyridine in 10 mL of nitromethane were added. The solution was stirred at 60° C. for 3 h, diluted with EtOAc and 1M KHSO4. The inorganic phase was extracted with EtOAc, the combined organic phases were washed with a saturated aqueous solution of NaHCO3, brine and were dried over Na2SO4 and evaporated. Column chromatography on silica gel with EtOAc/n-hexane 1:3 gave 1.2 g (95%) of trans-3-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid methyl ester as light yellow oil, MS: 424 (MH+).

後処理

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in 5 mL of nitromethane
  3. stirringThe solution was stirred at 60° C. for 3 h
  4. extractionThe inorganic phase was extracted with EtOAc
  5. washthe combined organic phases were washed with a saturated aqueous solution of NaHCO3, brine
  6. dry with materialwere dried over Na2SO4
  7. customevaporated

出典と根拠

ORDレコード
ord-0ab0dbe7d73b40679dc1f0b713d0a990
出典データセット
uspto-grants-2005_11
特許番号
US06965048B2

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