Water → HCID 52951813, compound

HRID 2273635Notes

Reaction equation

HRID 2273635 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20].O>C(OCC)(=O)C>[CH3:18][S:19]([O:10][CH2:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 52951681HCID 52951681, compound

Product 1

HCID 52951813HCID 52951813, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 42 (6.50 g, 46.1 mmol) in anhydrous ethyl acetate (250 mL) were added successively at 0° C., under argon, triethylamine (6.40 mL, 46.0 mmol) and dropwise methanesulfonyl chloride (3.60 mL, 46.5 mmol). The mixture was stirred at 0° C. for 10 min before addition of water (200 mL) at room temperature. The mixture was extracted with ethyl acetate (3×200 mL). The organic layers were combined, dried on magnesium sulfate, filtered and evaporated under vacuum. The residue was chromatographed (Al2O3, CH2Cl2) to give sulfonate 43 (7.56 g, 34.5 mmol) as a yellow oil. Yield 75%; Rf (Al2O3, CH2Cl2) 0.52; IR (CCl4) ν 1179, 1352, 1414, 1613 cm−1; 1H NMR (200 MHz, CDCl3) δ 2.95 (s, 3H), 3.09 (t, 2H, J=6.4 Hz), 4.45 (t, 2H, J=6.4 Hz), 6.82 (s, 1H), 7.07 (d, 1H, J=5.1 Hz), 8.15 (d, 1H, J=5.1 Hz); MS m/z 219 (M+, 3), 123 (100), 111 (30), 83 (14), 79 (53), 57 (11).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  2. customdried on magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was chromatographed (Al2O3, CH2Cl2)

Sources & evidence

ORD record
ord-306a72dc6b804b6db3b004a2b3bbc06a
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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