Nitrogen → HCID 57250906, 화합물

HRID 234727노트

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HRID 234727 반응식
[OH:1][C@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:4](=[CH:5][C:6](=[O:29])[C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.N#N.FC(F)(F)S(O[Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])(=O)=O>C(Cl)Cl>[O:29]=[C:6]1[CH:5]=[C:4]2[C@:24]([CH3:27])([CH2:25][CH2:26][C@H:2]([O:1][Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])[CH2:3]2)[C@@H:23]2[C@@H:7]1[C@H:8]1[C@:20]([CH3:28])([CH2:21][CH2:22]2)[C@@H:11]([C@H:12]([CH3:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:9]1

참가 물질

5

반응물 3

HCID 947NitrogenHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 23250094Methyl (3β)-3-hydroxy-7-oxochol-5-en-24-oate

생성물 1

HCID 57250906HCID 57250906, 화합물수율 84.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of methyl 313-hydroxy-7-oxochol-5-en-24-oate (2) (5.02 g, 12.5 mmoles) and 2,6-1utidine (3.32 ml, 28.5 mmoles) in CH2Cl2 (23 ml) cooled in an ice bath in a N2 atmosphere was added dropwise with magnetic stirring triisopropylsilyl trifluoromethanesulfonate (4.56 g, 17 mmoles). After 2 hrs, the reaction was diluted with CH2Cl2 (150 ml). It was then washed with cold 2N HCl, washed twice with H2O and then with saturated brine before drying with MgSO4. Evaporation in vacuo and purification of the residue by flash chromatography on silica gel with hexane-EtOAc (10:1 ) gave 5.88 g of 3 as a colorless syrup. NMR (CDCl3): δ0.67 (s, 3H, 18-Me); 0.93 (d, 3H, 20-Me); 1.06 (s, 18H, TIPS Me); 1.19 (s, 3H, 19-Me); 3.66 (s, 3H, CO2Me); 3.68 (m, 1H, 3-H); 5.66 (s, 1H, 6-H).

후처리

  1. additionwas added dropwise
  2. washIt was then washed with cold 2N HCl
  3. washwashed twice with H2O
  4. dry with materialwith saturated brine before drying with MgSO4
  5. customEvaporation
  6. customin vacuo and purification of the residue by flash chromatography on silica gel with hexane-EtOAc (10:1 )

출처 및 근거

ORD 기록
ord-e79937d60d984ae6b527a3f8319d44e9
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05595996

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