Sodium Cyanide → HCID 15374516, 화합물

HRID 1826101노트

반응식

HRID 1826101 반응식
[Li][C:2]#[N:3].C1(C)C=CC(S(O[CH2:14][C@H:15]([OH:26])[CH2:16][C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)(=O)=O)=CC=1.[C-]#N.[Na+]>CN(C=O)C>[OH:26][C@H:15]([CH2:16][C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][C:2]#[N:3]

참가 물질

5

반응물 3

HCID 8929Sodium CyanideHCID 53647276(R)-3-indol-2-yl-2-hydroxypropanyl p-toluenesulfonateHCID 178506913HCID 178506913, 화합물

생성물 1

HCID 15374516HCID 15374516, 화합물수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 0.5 M LiCN in DMF (30 mL) was added (R)-3-indol-2-yl-2-hydroxypropanyl p-toluenesulfonate (R)-2 (5.6 g, 16.2 mmol) and sodium cyanide (1.5 g, 30.6 mmol). The reaction mixture was stirred for 1 hour at 100° C., cooled to room temperature, poured into 80 mL ice-water, and extracted with ethyl acetate (3×50 mL). The combined organic solution was washed with saturated sodium bicarbonate (2×50 mL), brine (2×30 mL), dried over anhydrous sodium sulfate, and evaporated to yield a deep red oil. The oil was purified by flash chromatography (hexane:ethyl acetate 2:3) to give 2.4 g (74%) of the title compound as a light yellow solid.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic solution was washed with saturated sodium bicarbonate (2×50 mL), brine (2×30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto yield a deep red oil
  7. customThe oil was purified by flash chromatography (hexane:ethyl acetate 2:3)

출처 및 근거

ORD 기록
ord-f5eada18cec14cddb4a5893103b5170e
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049432B2

반응 노트

불러오는 중…