Methanesulfonyl chloride → HCID 22170443, compound

HRID 736380Notes

Reaction equation

HRID 736380 reaction equation
[C:1]([NH:4][C:5]1[C:6]([C:11]2[CH:29]=[CH:28][C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=3)=[O:16])=[CH:13][CH:12]=2)=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Li]CCCC.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>O1CCCC1>[C:1]([N:4]([S:36]([CH3:35])(=[O:38])=[O:37])[C:5]1[C:6]([C:11]2[CH:29]=[CH:28][C:14]([C:15]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]([CH3:25])([CH3:27])[CH3:26])=[CH:22][CH:23]=3)=[O:16])=[CH:13][CH:12]=2)=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 11361213HCID 11361213, compoundHCID 178418339Butyllithium

Product 1

HCID 22170443HCID 22170443, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

The product from Example 5 (610 mg, 1.58 mmol) in tetrahydrofuran (10 mL) was treated with n-BuLi (1.1 mL, 1.6 M in hexanes, 1.76 mmol) dropwise at −10° C. The reaction mixture was stirred at −10° C. for 15 minutes and then treated with methanesulfonyl chloride (0.13 mL, 1.68 mmol). The mixture was allowed to gradually warm to room temperature and stir overnight, quenched with H2O (10 mL), and diluted with ethyl acetate (50 mL). The layers were separated and the organic layer was washed with H2O (2×10 mL) and brine (10 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluant gradient from 99:1 CH2Cl2:CH3OH to 97:3 CH2Cl2:CH3OH) to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.29 (s, 1H), 8.81 (dd, J=4.7 Hz, 1.7 Hz, 1H), 8.15 (dd, J=8.2 Hz, 1.7 Hz, 1H), 8.07 (m, 2H), 7.62-7.73 (m, 5H), 7.35-7.40 (m, 2H), 3.30 (s, 3H), 2.01 (s, 3H), 1.29 (s, 9H); MS (ESI+) m/z δ 466 (M+H)+.

Workup

  1. temperatureto gradually warm to room temperature
  2. stirringstir overnight
  3. customquenched with H2O (10 mL)
  4. additiondiluted with ethyl acetate (50 mL)
  5. customThe layers were separated
  6. washthe organic layer was washed with H2O (2×10 mL) and brine (10 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated under reduced pressure
  10. customThe residue was purified by chromatography on silica gel (eluant gradient from 99:1 CH2Cl2:CH3OH to 97:3 CH2Cl2:CH3OH)

Sources & evidence

ORD record
ord-a5e696d3f10748cfa25bb5612f81f36b
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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