Triethylamine → HCID 70975477, compound

HRID 2199364Notes

Reaction equation

HRID 2199364 reaction equation
[CH:1]([CH:13]1[CH2:18][C:17](=[O:19])[O:16][C:14]1=[O:15])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C.[F:27][C:28]1[CH:49]=[CH:48][CH:47]=[CH:46][C:29]=1[CH:30]=[C:31]1[C:36](=[O:37])[C:35](=[CH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[F:45])[CH2:34][NH:33][CH2:32]1>C(Cl)Cl>[F:45][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[CH:38]=[C:35]1[C:36](=[O:37])[C:31](=[CH:30][C:29]2[CH:46]=[CH:47][CH:48]=[CH:49][C:28]=2[F:27])[CH2:32][N:33]([C:14]([CH:13]([CH:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:18][C:17]([OH:16])=[O:19])=[O:15])[CH2:34]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 329333-(1-Dodecen-1-yl)dihydro-2,5-furandioneHCID 66993057HCID 66993057, compound

Product 1

HCID 70975477HCID 70975477, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dodecenyl succinic anhydride (179 mg, 0.67 mmol) and triethylamine (0.18 ml, 1.29 mmol) were added to a solution of compound 1 (200 mg, 0.64 mmol) in dry methylene chloride and stirred at room temperature for 2 h. The mixture was chromatographed on a silica column, and the title compound 26 was eluted from the column using 10% methanol:chloroform as eluant. The compound 26 was obtained as yellow thick syrup (352 mg, 95% yield). Rf (10:90 methanol:chloroform)=0.26. 1H NMR (300 MHz, CDCl3): δ 7.90-7.80 (m, 3H, 2C═CH, vinyl-H), 7.42-7.00 (m, 9H, Ar—H, vinyl-H), 5.30-5.05 (m, 4H), 5.00-4.95 (m, 2H), 4.82-7.78 (m, 2H), 4.65-4.40 (m, 4H), 2.85-2.70 (m, 2H), 2.50-2.40 (m, 2H), 2.30-2.10 (m, 4H), 2.08-1.90 (m, 4H), 1.90-1.70 (m, 2H), 0.91 (t, 3H, J=6.4, CH3). 13C NMR (75 MHz, CDCl3): δ 185.81, 173.27, 170.15, 161.96 (d, J=55.2), 159.45 (d, J=53.7), 135.38, 134.29, 133.30, 133.10, 131.52, 130.78, 130.51, 125.33, 124.78, 124.23 (d, J=3.1), 122.47 (d, J=13.3), 122.22 (d, J=14.8), 116.32 (d, J=18.9), 116.22 (d, J=21.8), 115.93 (d, J=25.7), 46.45 (d, J=3.2), 46.48 (d, J=3.1), 35.27, 33.08, 31.92, 29.9, 29.19, 29.44, 29.16, 28.86, 25.05, 24.21, 22.67, 14.13. ESI Mass calculated for C35H41F2NNaO4 (M+Na)+600.29. found 600.20.

Workup

  1. customThe mixture was chromatographed on a silica column
  2. washthe title compound 26 was eluted from the column

Sources & evidence

ORD record
ord-c0f19d08f7de44d2b602e7b546d66524
Source dataset
uspto-grants-2016_06
Patent number
US09359196B2

Reaction notes

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