Undec-4-ene → HCID 68428408, compound

HRID 1716807Notes

Reaction equation

HRID 1716807 reaction equation
C1C2C(C[O:15][C:16]([CH2:18][S:19]([NH:22][N:23]3[CH2:27][CH:26]([C:28]4[CH:33]=[CH:32][C:31]([CH:34]5[CH2:36][CH2:35]5)=[CH:30][CH:29]=4)[N:25]([CH2:37][CH2:38][C:39]4[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=4)[C:24]3=[O:47])(=[O:21])=[O:20])=[O:17])C3C(=CC=CC=3)C=2C=CC=1.CCCCCCC=CCCC>CN(C=O)C>[CH:34]1([C:31]2[CH:32]=[CH:33][C:28]([CH:26]3[CH2:27][N:23]([NH:22][S:19]([CH2:18][C:16]([OH:17])=[O:15])(=[O:21])=[O:20])[C:24](=[O:47])[N:25]3[CH2:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=3)=[CH:29][CH:30]=2)[CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 136496Undec-4-eneHCID 68426121HCID 68426121, compound

Product 1

HCID 68428408HCID 68428408, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[[(9H-fluoren-9-ylmethyloxy)carbonylmethyl]sulfonylamino]-3-[2-(4-methoxyphenyl)ethyl]-4-(4-cyclopropylphenyl)-2-imidazolidinone (2.0 g, 0.0031 mol) in DMF (15 mL) at room temperature is added 1,8-diazabycyclo[5.4.0]undec-7-ene (0.35 mL). The reaction is stirred for approximately one hour, diluted with ice-cold 0.1 N HCl and extracted with ethyl acetate. The organic phase is washed with brine, dried (sodium sulfate) and concentrated. The residue is warmed in approximately 20 mL of ether and diluted slowly with approximately 20 mL of hexanes. The liquid is decanted and the resulting material is dried under vacuum to afford 1.08 g of the desired compound. 1H NMR (CDCl3) δ 8.03 (bs, 1H), 7.19 (d, J=8.4 Hz, 2H), 7.11 (d, J=8.1 Hz, 2H), 7.05 (m, 2H), 6.84 (m, 2H), 4.51 (t, J=8.4 Hz, 1H), 4.30 (s, 2H), 4.01 (t, J=8.7, 1H), 3.81 (s, 3H), 3.66 (m, 1H), 3.51 (m, 1H), 2.95 (m, 1H), 2.64 (m, 1H), 1.93 (m, 1H), 1.02 (m, 2H), 0.74 (m, 2H). MS 652 (MH+). Anal. calcd. for C23H27N3O6S ¼C4H10O: C, 58.58; H, 6.04; N, 8.54. Found: C, 58.37; H, 6.01; N, 8.35.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. temperatureThe residue is warmed in approximately 20 mL of ether
  6. additiondiluted slowly with approximately 20 mL of hexanes
  7. customThe liquid is decanted
  8. customthe resulting material is dried under vacuum

Sources & evidence

ORD record
ord-8e8d60e7dea44422b7a2eadf21bfb6ca
Source dataset
uspto-grants-2010_09
Patent number
US07803827B2

Reaction notes

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