Stannous chloride dihydrate → HCID 58930583, compound

HRID 852927Notes

Reaction equation

HRID 852927 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]2[S:25][C:26]3[CH:32]=[C:31]([N+:33]([O-])=O)[CH:30]=[CH:29][C:27]=3[N:28]=2)=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl.C([O-])(=[O:44])C.[NH4+]>C1COCC1.CO.O>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:44])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]2[S:25][C:26]3[CH:32]=[C:31]([NH2:33])[CH:30]=[CH:29][C:27]=3[N:28]=2)=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 517165Ammonium AcetateHCID 86601380HCID 86601380, compound

Product 1

HCID 58930583HCID 58930583, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a suspension of compound 141 (200 mg, 0.385 mmol) in a mixture of THF/MeOH/H2O (10 mL/10 mL/10 mL) were successively added tin(II) chloride dihydrate (1.35 g, 8.46 mmol) and ammonium acetate (1.09 g, 14.12 mmol). The mixture was refluxed for 2 days, the tin salts were filtered off and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc and H2O (brine was added to break the emulsion). Organic phase was successively washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, and concentrated in vacuo to afford the title compound 143 (145 mg, 77% yield). 1H NMR: (DMSO-d6) δ (ppm): 12.89 (bs, 1H), 10.79 (s, 1H), 8.12 (d, J=2.0 Hz, 1H), 8.05 (d, J=8.8 Hz, 2H), 7.90-7.68 (m, 3H), 7.62 (d, J=8.4 Hz, 2H), 7.48 (bs, 1H), 7.21 (dd, J=4.9, 3.7 Hz, 1H), 4.65 (s, 2H). m/z: 490.5 (MH+).

Workup

  1. temperatureThe mixture was refluxed for 2 days
  2. filtrationthe tin salts were filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between EtOAc and H2O (brine
  5. additionwas added
  6. washOrganic phase was successively washed with saturated aqueous NaHCO3 and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7fb2156835c4404a018299ca32596a7
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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