Hydrochloric Acid → HCID 68842563, compound

HRID 660512Notes

Reaction equation

HRID 660512 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si](C(C)(C)C)(C)C)[CH:12]=[CH:11][C:10]=1[N:23]1[S:27](=[O:29])(=[O:28])[N:26]([CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:25](=[O:36])[CH2:24]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1.O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[N:23]1[S:27](=[O:28])(=[O:29])[N:26]([CH2:30][CH2:31][Si:32]([CH3:34])([CH3:33])[CH3:35])[C:25](=[O:36])[CH2:24]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68837989HCID 68837989, compound

Product 1

HCID 68842563HCID 68842563, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-[2-benzyloxy-4-(tert-butyldimethylsilanyloxy)phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (100 mg, 0.18 mmol) in THF (4.5 mL) is added 0.5 mL of 4N HCl in dioxane and the mixture is stirred at RT for 5 days. The solution is concentrated, dissolved in EtOAc and the aqueous phase separated. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure to afford the title compound: 1H NMR (CDCl3δ7.29 (m, 5H), 7.16 (d, J=8.3 Hz, 1H), 6.42 (d, J=2.5 Hz, 1H), 6.27 (dd, J=8.3, 2.5 Hz, 1H), 4.92 (s, 2H), 4.24 (s, 2H), 3.52 (m, 2H), 0.99 (m. 2H), 0.00 (s, 9H): (M+1)+=435.

Workup

  1. concentrationThe solution is concentrated
  2. dissolutiondissolved in EtOAc
  3. customthe aqueous phase separated
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8f5101d5105441e697201d480c37f6b6
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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