Tin tetrachloride → HCID 136173388, 화합물

HRID 2191047노트

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HRID 2191047 반응식
[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:23])[C:8]2[N:9]=[CH:10][N:11]([C:21]=2[N:22]=1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)(=[O:3])[CH3:2].[C:24]([O:32][C@@H:33]1[C@H:37]([F:38])[C@@H:36]([CH2:39][CH:40]([P:48]([O:53][CH2:54][CH3:55])([O:50][CH2:51][CH3:52])=[O:49])[S:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:35][C@H:34]1OC(=O)C)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl.ClCCCl>[C:24]([O:32][C@@H:33]1[C@H:37]([F:38])[C@@H:36]([CH2:39][CH:40]([P:48]([O:53][CH2:54][CH3:55])([O:50][CH2:51][CH3:52])=[O:49])[S:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:35][C@H:34]1[N:11]1[CH:10]=[N:9][C:8]2[C:7](=[O:23])[NH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:22][C:21]1=2)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

6

반응물 3

HCID 24287Tin tetrachlorideHCID 86641126HCID 86641126, 화합물HCID 135440620N-Acetyl Guanosine

생성물 1

HCID 136173388HCID 136173388, 화합물수율 30%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매2회

실험 절차

N-Acetyl Guanosine (108 mg, 0.56 mmol) was suspended in 10 mL anhydrous CH2Cl2. With stirring under nitrogen, BSA (345 mg, 1.4 mmol) was added to the suspension. The mixture was stirred at 80° C. for 2 h and cooled to r.t. Compound 35.14 (200 mg, 0.37 mmol) in 5 mL anhydrous DCE was added to the mixture, followed by SnCl4 (64 mL, 0.55 mmol). The mixture was heated to 65° C. for 6 h and then cooled to r.t., diluted with 50 mL CH2Cl2 and poured onto a mixture of 50 g ice/50 mL saturated Rochelles Salt. The mixture was stirred for another 1 h. The organic layer was separated and the aqueous layer was extracted with 100 mL additional CH2Cl2. The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 5% MeOH in CH2Cl2 to give compound 35.15 (73 mg, 30% yield).

후처리

  1. additionBSA (345 mg, 1.4 mmol) was added to the suspension
  2. stirringThe mixture was stirred at 80° C. for 2 h
  3. temperatureThe mixture was heated to 65° C. for 6 h
  4. temperaturecooled to r.t.
  5. stirringThe mixture was stirred for another 1 h
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with 100 mL additional CH2Cl2
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. washeluting with 5% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-023007433d13415fb4edd9d69980b512
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324179B2

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