Trimethylsilyl iodide → HCID 86762223, compound

HRID 1619041Notes

Reaction equation

HRID 1619041 reaction equation
[C:1]([NH:9][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][C@:14]2([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[Si](C)(C)C>C(#N)C>[S:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C@:14]12[CH2:16][NH:17][CH2:18][C@H:13]1[CH2:12][S:11][C:10]([NH:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[N:15]2

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86762220benzyl(4aR,7aR)-2-benzamido-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Product 1

HCID 86762223HCID 86762223, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of benzyl (4aR,7aR)-2-benzamido-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (14 g, 29.3 mmol) in acetonitrile (210 mL) is treated with iodotrimethylsilane (7.53 mL, 52.7 mmol) at room temperature. The solution is stirred for 1 hour and the solvent is evaporated. The residue is quenched with 1 M hydrochloric acid and ethyl acetate and the resulting mixture is filtered through diatomaceous earth. The aqueous layer is separated, neutralized with 50% w/w aqueous solution of sodium hydroxide and extracted with ethyl acetate. The organic extracts are dried over sodium sulfate and concentrated to give the title compound (7.9 g, 78%). ES/MS (m/e): 344 (M+H).

Workup

  1. customthe solvent is evaporated
  2. customThe residue is quenched with 1 M hydrochloric acid and ethyl acetate
  3. filtrationthe resulting mixture is filtered through diatomaceous earth
  4. customThe aqueous layer is separated
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic extracts are dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-985ac0a9e1f845e68adfa138e782f99e
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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