Tetrahydrofuran → HCID 57495376、化合物

HRID 1362552ノート

反応式

HRID 1362552 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

HCID 57495376HCID 57495376、化合物収率 89.5%

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b9a8ee31f8f9431e8430711c3f45dbae
出典データセット
uspto-grants-2011_02
特許番号
US07880020B2

反応ノート

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