Trimethylsilyl iodide → HCID 15950040, compound

HRID 548766Notes

Reaction equation

HRID 548766 reaction equation
C[Si](I)(C)C.[CH3:6][C@H:7]([O:11][C:12]1[CH:13]=[C:14]([CH:24]=[C:25]([O:27][C:28]2[CH:40]=[CH:39][C:31]3[C:32](=[O:38])[N:33]([CH3:37])[CH2:34][CH2:35][O:36][C:30]=3[CH:29]=2)[CH:26]=1)[C:15]([NH:17][C:18]1[S:22][N:21]=[C:20]([CH3:23])[N:19]=1)=[O:16])[CH2:8][O:9]C.C(=O)([O-])O.[Na+]>C(#N)C>[OH:9][CH2:8][C@@H:7]([O:11][C:12]1[CH:13]=[C:14]([CH:24]=[C:25]([O:27][C:28]2[CH:40]=[CH:39][C:31]3[C:32](=[O:38])[N:33]([CH3:37])[CH2:34][CH2:35][O:36][C:30]=3[CH:29]=2)[CH:26]=1)[C:15]([NH:17][C:18]1[S:22][N:21]=[C:20]([CH3:23])[N:19]=1)=[O:16])[CH3:6]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 15950036HCID 15950036, compound

Product 1

HCID 15950040HCID 15950040, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl iodide (0.95 mL, 6.7 mmol) was added to a solution of 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide (335 mg, 0.67 mmol) in acetonitrile (20 mL) under an atmosphere of argon and the mixture stirred at RT for 18 hours. The mixture was poured onto saturated sodium hydrogen carbonate solution (50 mL), the acetonitrile removed in vacuo, and the aqueous layer extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with sodium thiosulphate solution, brine, dried (MgSO4) and evaporated in vacuo to a residue which was chromatographed on silica, eluting with ethyl acetate then with 2% methanol in DCM, to give the desired compound as a colourless solid (50 mg). 1H NMR δ (CDCl3): 1.3 (d, 3H), 2.5 (s, 3H), 3.2 (s, 3H), 3.6 (t, 2H), 3.75 (m, 2H), 4.4 (t, 2H), 4.55 (m, 1H), 6.55 (d, 1H), 6.7 (dd, 1H), 6.8 (d, 1H), 7.2 (s, 1H), 7.25 (s, 1H), 7.85 (d, 1H); m/z 485 (M+H)+

Workup

  1. customthe acetonitrile removed in vacuo
  2. extractionthe aqueous layer extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with sodium thiosulphate solution, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo to a residue which
  6. customwas chromatographed on silica
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f0b0312a79f4404999417f98b94daa67
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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