Dimethyl Sulfate → HCID 178495813, compound

HRID 255130Notes

Reaction equation

HRID 255130 reaction equation
[CH2:1]1[CH:8]2[C:4]3([C:10]([N:12]=[C:13]4[N:17]([CH2:18]O)[CH:16]=[CH:15][S:14]4)=[O:11])[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2.C[C:21](C)([O-:23])C.[K+].S(OC)(O[CH3:30])(=O)=O.[O:33]1[CH2:37]CC[CH2:34]1>>[CH3:34][O:33][CH2:37][CH2:18][N:17]1[CH:16]=[C:15]([CH2:30][O:23][CH3:21])[S:14]/[C:13]/1=[N:12]\[C:10]([C:4]12[CH2:5][CH:6]3[CH2:9][CH:2]([CH2:1][CH:8]1[CH2:7]3)[CH2:3]2)=[O:11]

Participants

5

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 66860750HCID 66860750, compound

Product 1

HCID 178495813HCID 178495813, compound

Conditions

Temperature
75 °C

Procedure

To a solution of Example 140C (120 mg, 0.34 mmol) in tetrahydrofuran (5 mL) were added potassium tert-butoxide (83 mg, 0.75 mmol) and dimethyl sulfate (95 mg 0.75 mmol). The reaction mixture was stirred at 75° C. for 16 hours, then cooled, quenched with saturated aqueous NaHCO3 (5 mL) and extracted with ethyl acetate (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.54-1.70 (m, 4 H), 1.73-1.92 (m, 4 H), 2.13-2.24 (m, 2 H), 2.30 (s, 1 H), 2.67 (t, J=6.8 Hz, 2 H), 3.33 (s, 3 H), 3.36 (s, 3 H), 3.64-3.73 (m, 2 H), 4.22-4.30 (m, 2 H), 4.42 (s, 2 H), 6.95 (s, 1 H); MS (ESI+) m/z 351 (M+H)+; Anal. Calculated for C18H26N2O3S: C, 61.69; H, 7.48; N, 7.99. Found: C, 61.93; H, 7.62; N, 7.68.

Workup

  1. temperaturecooled
  2. customquenched with saturated aqueous NaHCO3 (5 mL)
  3. extractionextracted with ethyl acetate (2×10 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fe875cd8b35c415ea518ef3f14dd67b4
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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