Isopropyl iodide → HCID 67812068, compound

HRID 2401396Notes

Reaction equation

HRID 2401396 reaction equation
[CH3:1][C:2]1[S:24][C:5]2[C:6]3[C:22]([CH3:23])=[N:21][O:20][C:7]=3[C@H:8]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:9][C:10](=[O:11])[C:4]=2[C:3]=1[CH3:25].S1C=[CH:29][CH:28]=[CH:27]1.IC(C)C>C1(C)C=CC=CC=1.[Ag]=O>[CH:28]([O:11][C:10]1[C:4]2[C:3]([CH3:25])=[C:2]([CH3:1])[S:24][C:5]=2[C:6]2[C:22]([CH3:23])=[N:21][O:20][C:7]=2[C@H:8]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:9]=1)([CH3:29])[CH3:27]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 8030ThiopheneHCID 67813157HCID 67813157, compound

Product 1

HCID 67812068HCID 67812068, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl 2-((6S)-2,3,9-trimethyl-4-oxo-5,6-dihydro-4H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)acetate (17 wherein ring A is thiophene; 100 mg, 0.276 mmol), silver oxide (70 mg, 0.304 mmol) and 2-iodopropane (61 mg, 0.359 mmol) in toluene (5 mL) was heated to 90° C., and stirred overnight. After cooling to room temperature, the reaction mixture was evaporated to dryness and the residue was purified by flash chromatography eluting with petroleum ether/ethyl acetate=5:1 to give tert-butyl 2-((6S)-4-isopropoxy-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)acetate as a yellow solid (80 mg, 72% yield). LC/MS m/z 404 [M+1-1]+; 1H NMR (300 MHz, CDCl3) δ 5.30-5.03 (m, 1H), 4.51 (t, J=6 Hz, 1H), 3.11-3.08 (m, 2H), 2.43 (s, 3H), 2.39 (s, 3H), 2.26 (s, 3H), 1.46 (s, 9H), 1.30 (d, J=6 Hz, 3H), 1.20 (d, J=6 Hz, 3H).

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. customthe residue was purified by flash chromatography
  3. washeluting with petroleum ether/ethyl acetate=5:1

Sources & evidence

ORD record
ord-086ee83fa0ed430cadda05e6ab4538f0
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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