Methanol → HCID 70975542, compound

HRID 2199365Notes

Reaction equation

HRID 2199365 reaction equation
[CH:1]([CH:15]1[CH2:20][C:19](=[O:21])[O:18][C:16]1=[O:17])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(N(CC)CC)C.[F:29][C:30]1[CH:51]=[CH:50][CH:49]=[CH:48][C:31]=1[CH:32]=[C:33]1[C:38](=[O:39])[C:37](=[CH:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[F:47])[CH2:36][NH:35][CH2:34]1.CO>C(Cl)Cl.C(Cl)(Cl)Cl>[F:47][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[CH:40]=[C:37]1[C:38](=[O:39])[C:33](=[CH:32][C:31]2[CH:48]=[CH:49][CH:50]=[CH:51][C:30]=2[F:29])[CH2:34][N:35]([C:16]([CH:15]([CH:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:20][C:19]([OH:18])=[O:21])=[O:17])[CH2:36]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 227803HCID 227803, compoundHCID 66993057HCID 66993057, compound

Product 1

HCID 70975542HCID 70975542, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Tetradecenyl succinic anhydride (198 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 methylene chloride. The reaction mixture was stirred at room temperature for 2 h. The crude compound was passed through silica column, and using 10% methanol:chloroform as eluant, compound 27 was obtained as yellow thick syrup (357 mg, 92% yield). Rf (10:90 methanol:chloroform)=0.31. 1H NMR (300 MHz, CDCl3): δ 7.90-7.80 (m, 3H, 2C═CH, vinyl-H), 7.45-7.00 (m, 9H, Ar—H, vinyl-H), 5.40-4.50 (m, 9H), 2.70-1.70 (m, 9H), 1.40-1.20 (m, 12H), 0.93 (t, 3H, J=6.6, CH3). 13C NMR (75 MHz, CDCl3): δ 186.10, 174.03, 170.76, 162.6 (d, J=51.2), 133.75, 133.55, 132.36, 130.75, 126.68, 124.22 (d, J=9.8), 115.98 (d, J=21.2), 44.75, 32.46, 31.90, 22.67, 14.12. ESI Mass calculated for C37H45F2NNaO4 (M+Na)+628.32. found 628.27.

Sources & evidence

ORD record
ord-afa6e0e1d15f42e29524e522a78a6ee9
Source dataset
uspto-grants-2016_06
Patent number
US09359196B2

Reaction notes

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