Methanol → HCID 25160450, compound

HRID 2198265Notes

Reaction equation

HRID 2198265 reaction equation
O.O[O:3][S:4]([O-:6])=O.[K+].[CH2:8]1[CH:15]2[C:11]3([C:17]([NH:19][C:20]4[S:28][C:23]5[CH2:24][O:25][CH2:26][CH2:27][C:22]=5[C:21]=4[C:29]([NH:31][CH2:32][CH2:33]SC)=[O:30])=[O:18])[CH2:12][CH:13]([CH2:16][CH:9]1[CH2:10]3)[CH2:14]2.[CH3:36]O>>[CH2:14]1[CH:15]2[C:11]3([C:17]([NH:19][C:20]4[S:28][C:23]5[CH2:24][O:25][CH2:26][CH2:27][C:22]=5[C:21]=4[C:29]([NH:31][CH2:32][CH2:33][S:4]([CH3:36])(=[O:6])=[O:3])=[O:30])=[O:18])[CH2:10][CH:9]([CH2:16][CH:13]1[CH2:12]3)[CH2:8]2

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 25160319HCID 25160319, compound

Product 1

HCID 25160450HCID 25160450, compound

Conditions

Temperature
0 °C

Procedure

To a 50-mL round-bottomed flask containing a magnetic stir bar were added water (2 mL) and OXONE® (155 mg, 0.252 mmol). The flask was cooled in an ice bath. A solution of Example 201 in methanol (11 mL) was added and the resulting slurry was stirred at 0° C. for 30 minutes. The mixture was allowed to warm to room temperature over 3 hours. The mixture was extracted with dichloromethane (3×5 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated by rotary evaporator. The crude material was recrystallized from ethyl acetate/hexanes to afford the title compound. 1H NMR (dimethylsulfoxide-d6, 300 MHz) δ 1.62-1.67 (m, 4H), 1.76-1.88 (m, 4H), 1.98-2.02 (m, 2H), 2.33 (br s, 2H), 2.59-2.63 (m, 1H), 2.84 (t, J=4.8 Hz, 2H), 3.05 (s, 3H), 3.39 (t, J=6.6 Hz, 2H), 3.69-3.75 (m, 2H), 3.84 (t, J=5.4 Hz, 2H), 4.65 (br s, 2H), 7.48 (t, J=5.8 Hz, 1H), 11.94 (br s, 1H). MS (ESI+) m/z 453.1 (M+H)+. Anal. calcd. for C21H28N2O5S2: C, 55.73; H, 6.24; N, 6.19. Found: C, 55.76; H, 6.25; N, 6.10.

Workup

  1. additionTo a 50-mL round-bottomed flask containing a magnetic stir bar
  2. temperatureThe flask was cooled in an ice bath
  3. temperatureto warm to room temperature over 3 hours
  4. extractionThe mixture was extracted with dichloromethane (3×5 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporator
  8. customThe crude material was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7f8b9680ce004755a305d8e20db5acba
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

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