Hexane → Ethyl acetate hexane

HRID 1984042Notes

Reaction equation

HRID 1984042 reaction equation
CN[C:3]1[CH:11]=[CH:10][C:6](C(Cl)=O)=[CH:5][C:4]=1S(N1CCOCC1)(=O)=O.C(N(CC)CC)C.CCCCCC.[C:34]([O:37][CH2:38][CH3:39])(=[O:36])[CH3:35]>ClCCl>[CH3:10][CH2:11][CH2:3][CH2:4][CH2:5][CH3:6].[C:34]([O:37][CH2:38][CH3:39])(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 57713927HCID 57713927, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Methylamino)-3-(morpholinosulfonyl)benzoyl chloride (1.4.Aa, 100 mg, 1.5 eq) was dissolved in 8 mL of dry dichloromethane. Next, S-fenchyl amine (prepared as reported in FR96/01953) (Bb, 0.032 mL, 1 eq) was added. Triethylamine (0.030 mL, 1 eq) was then added. The progress of the reaction was monitored by TLC in 85% ethyl acetate:hexane. After 45 minutes the product was washed with H2O, 1.0 M HCl, and brine. The dichloromethane was evaporated and crystals were obtained. The crude product 1A was purified on a silica gel column using hexane/ethyl acetate [66 mg of purified product was obtained (72% yield)]. MS analysis (m+1)=436.6. 1H NMR (CDCl3), δ 0.84 (s, 3H), 1.10 (s, 3H), 1.18 (s, 3H), 1.26 (m, 3H), 1.51 (m, 1H), 1.61 (s, 2H), 1.72 (d, 2H), 1.81 (m, 1H), 2.91 (d, J=5 Hz, 3H), 3.08 (t, J=5 Hz, 4H), 3.72 (t, J=5 Hz, 4H), 3.81 (dd, J=9 Hz and 2 Hz, 1H), 5.93 (d, J=9 Hz, 1H), 6.63 (d, J=5 Hz, 1H), 6.75 (d, J=9 Hz, 1H), 7.83 (q, J=8 Hz and 2 Hz, 1H), 8.02 (d, J=2 Hz, 1H).

Workup

  1. washAfter 45 minutes the product was washed with H2O, 1.0 M HCl, and brine
  2. customThe dichloromethane was evaporated
  3. customcrystals were obtained
  4. customThe crude product 1A was purified on a silica gel column

Sources & evidence

ORD record
ord-54f643614a5c4ac682e790e16bd71c28
Source dataset
uspto-grants-2009_06
Patent number
US07544676B2

Reaction notes

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