Trimethylsilyl iodide → HCID 15950038, compound

HRID 548763Notes

Reaction equation

HRID 548763 reaction equation
C[Si](I)(C)C.[CH3:6][C@H:7]([O:11][C:12]1[CH:13]=[C:14]([CH:25]=[C:26]([O:28][C:29]2[CH:41]=[CH:40][C:32]3[C:33](=[O:39])[N:34]([CH3:38])[CH2:35][CH2:36][O:37][C:31]=3[CH:30]=2)[CH:27]=1)[C:15]([NH:17][C:18]1[CH:23]=[N:22][C:21]([CH3:24])=[CH:20][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:25]=[C:26]([O:28][C:29]2[CH:41]=[CH:40][C:32]3[C:33](=[O:39])[N:34]([CH3:38])[CH2:35][CH2:36][O:37][C:31]=3[CH:30]=2)[CH:27]=1)[C:15]([NH:17][C:18]1[CH:23]=[N:22][C:21]([CH3:24])=[CH:20][N:19]=1)=[O:16])[CH3:6]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 15949952HCID 15949952, compound

Product 1

HCID 15950038HCID 15950038, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl iodide (0.35 mL, 2.4 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-(5-methylpyrazin-2-yl)benzamide (236 mg, 0.48 mmol) in acetonitrile (10 mL) under an atmosphere of argon and the mixture stirred at RT for 18 hours. The mixture was poured onto a saturated sodium hydrogen carbonate solution (25 mL), the acetonitrile removed in vacuo, and the aqueous layer extracted with ethyl acetate (3×25 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 1% methanol in ethyl acetate, to give the desired compound (107 mg).

Workup

  1. customthe acetonitrile removed in vacuo
  2. extractionthe aqueous layer extracted with ethyl acetate (3×25 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 1% methanol in ethyl acetate

Sources & evidence

ORD record
ord-4ab3325fa1a94708b4d28be20190cb6c
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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