Tin tetrachloride → HCID 136173388, compound

HRID 2191047Notes

Reaction equation

HRID 2191047 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 136173388HCID 136173388, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-023007433d13415fb4edd9d69980b512
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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