Isopropyl iodide → HCID 59485921, compound

HRID 1972280Notes

Reaction equation

HRID 1972280 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[C@H:11]([CH2:20][N:21]3[N:25]=[N:24][C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[N:22]3)[O:10][C:9]2=[O:32])=[CH:4][CH:3]=1.[C:33](=O)([O-])[O-].[K+].[K+].I[CH:40]([CH3:42])[CH3:41]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH:40]([CH3:42])[CH3:41])[CH:14]=3)[C@H:11]([CH2:20][N:21]3[N:25]=[N:24][C:23]([C:26]4[CH:27]=[N:28][C:29]([CH3:33])=[CH:30][CH:31]=4)=[N:22]3)[O:10][C:9]2=[O:32])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 59485723HCID 59485723, compound

Product 1

HCID 59485921HCID 59485921, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A small reaction tube fitted with screw cap containing a septa is charged with (4S,5S)-3-(4-chlorophenyl)-4-(3-hydroxyphenyl)-5-((5-(pyridin-3-yl)-2H-tetrazol-2-yl)-methyl)oxazolidin-2-one (25 mg, 0.055 mmol) and DMF (0.5 mL). Potassium carbonate (25 mg, 0.18 mmol) and 2-iodopropane (18 μL, 0.18 mmol) are then added and the vessel is heated to 50° C. for 4 h, then cooled to room temperature. The reaction is quenched with water, and extracted with EtOAc, dried over MgSO4, filtered and concentrated. The title compound is then obtained after flash chromatography (12 g Redisep, 30-50% EtOAc/hexanes). 1H NMR (acetone-d6, 400 MHz) δ 9.22 (br, s 1H), 8.72 (br, s, 1H), 8.33 (ddd, J=8.0, 1.8, 1.8 Hz, 1H), 7.52 (dd, J=7.9, 4.8 Hz, 1H), 7.46-7.42 (m, 2H), 7.32 (t, J=7.6 Hz, 1H), 7.27-7.24 (m, 2H), 7.09 (app t, J=1.9 Hz, 1H), 7.04 (d, J=7.7 Hz, 1H), 6.86 (ddd, J=8.3, 2.5, 0.8 Hz, 1H), 5.72 (d, J=5.0 Hz, 1H), 5.51 (dd, J=14.7, 5.9 Hz, 1H), 5.44 (dd, J=14.7, 4.1 Hz, 1H), 5.12 (ddd, J=5.8, 5.0, 4.2 Hz, 1H), 4.60 (septet, J=6.0 Hz, 1H), 1.24 (d, J=6.0 Hz, 3H, 1.21 (d, J=6.0 Hz, 3H); HPLC-MS calculated C25H23ClN6O3 (M+H+) 491.2, found 491.2.

Workup

  1. customA small reaction tube fitted with screw
  2. customcap
  3. additioncontaining a septa
  4. temperaturecooled to room temperature
  5. customThe reaction is quenched with water
  6. extractionextracted with EtOAc
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1faab2673c114559a29a400ab2da994e
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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