Iodide Ion → HCID 70200477, 화합물

HRID 1276488

반응식

HRID 1276488 반응식
[C:1]1([S:7]([N:10]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]([CH2:21]OS(C3C=CC=CC=3)(=O)=O)[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-:32]>CC(C)=O>[C:1]1([S:7]([N:10]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]([CH2:21][I:32])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 30165Iodide IonHCID 867561541-(Benzenesulfonyl)-3-(SR)-benzenesulfonyloxymethyl-4-(SR)-phenylpyrrolidine

생성물 1

HCID 70200477HCID 70200477, 화합물수율 96.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of 234 mg (0.51 mmol) of 1-(benzenesulfonyl)-3-(SR)-benzenesulfonyloxymethyl-4-(SR)-phenylpyrrolidine (from Example 1, Step D) and 1.1 g (7.7 mmol) of sodiuim iodide in 8 mL of acetone was heated at reflux for 20 h. The reaction mixture was partitioned between 50 mL of ether and 30 mL of H2O and the layers were separated. The organic layer was washed with 30 mL of sat'd NaCl and dried over MgSO4. The aqueous layers were combined and extracted with 30 mL of ether. The extract was dried; the organic layers were combined. and concentrated in vacuo. Flash chromatography on 25 g of silica gel using 3:2 v/v hexanes/ether as the eluant afforded 211 mg (96%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ2.43 (t, J=9.8, 1H), 2.64-2.74 (m, 2H), 3.30 (dd, J=2.5, 7.8, 1H), 3.47 (q, J=6.7, 1H), 3.67-3.74 (3H), 7.05-7.95 (1OH). Mass Spectrum (NH3-CI): m/z 428 (M+1).

후처리

  1. temperatureat reflux for 20 h
  2. customThe reaction mixture was partitioned between 50 mL of ether and 30 mL of H2O
  3. customthe layers were separated
  4. washThe organic layer was washed with 30 mL of sat'd NaCl
  5. dry with materialdried over MgSO4
  6. extractionextracted with 30 mL of ether
  7. customThe extract was dried
  8. concentrationand concentrated in vacuo

출처 및 근거

ORD 기록
ord-f466bd1aaae843c6860178b53a2e8d4d
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166037

연결된 노트

불러오는 중…