Tetrahydrofuran → HCID 57495376, compound

HRID 2099989Notes

Reaction equation

HRID 2099989 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([OH:16])=O)([O-:3])=[O:2].O1CCCC1.C(N(CC)CC)C.Cl.[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37]>>[CH3:39][O:38][C:36](=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][NH:30][C:14](=[O:16])/[CH:13]=[CH:12]/[CH:11]=[CH:10]/[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5357702(2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acidHCID 11499324Methyl 6-aminohexanoate hydrochloride

Product 1

HCID 57495376HCID 57495376, compoundYield 89.5%

Procedure

To a solution of (2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acid (9a) (0.44 g, 2.0 mmol) in dry tetrahydrofuran (10 ml) 1,1′-carbonyldiimidazole (0.36 g, 2.2 mmol) (Sigma-Aldrich) was added and the mixture was stirred for 1 hour at ambient temperature. To the reaction mixture triethylamine (0.30 g 3.0 mmol) and methyl 6-aminohexanoate hydrochloride (10) (0.40 g, 2.2 mmol) successively were added and the resultant suspension was stirred for 6 hour at ambient temperature. The solvent was evaporated, to the obtained residue water (15 ml) was added and the precipitate was filtered off. The precipitate was washed with an additional amount of water and dried to give the title compound (0.62 g, 89%) as a yellow solid, m.p. 115-117° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.10-1.79 (6H, m, CH2); 2.29 (2H, J=7.0 Hz, CH2); 3.17 (2H, q, J=5.6 Hz, CH2N);3.60 (3H, s); 6.24 (1H, d, J=14.8 Hz, CH); 7.04-8.10 (8H, m, CH—CH═CH, C6H4, NH).

Workup

  1. customThe solvent was evaporated, to the obtained residue water (15 ml)
  2. additionwas added
  3. filtrationthe precipitate was filtered off
  4. washThe precipitate was washed with an additional amount of water
  5. customdried

Sources & evidence

ORD record
ord-630c6cf2e98f4d3dbb844f734dcf01ff
Source dataset
uspto-grants-2009_08
Patent number
US07569724B2

Reaction notes

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