Water → 4-Methoxybenzoic acid, 6-aminohexyl ester

HRID 324109ノート

反応式

HRID 324109 の反応式
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]=[N+]=[N-])=[O:8])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[O:8])=[CH:19][CH:20]=1

参加物

6

反応物 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 865836674-Methoxybenzoic acid, 6-azidohexyl ester

生成物 1

HCID 572173864-Methoxybenzoic acid, 6-aminohexyl ester収率 78%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 4-methoxybenzoic acid, 6-azidohexyl ester (1.119 g, 4.035 mmol), triphenylphosphine (1.164 g, 4.439 mmol), and water (0.08 ml) in THF was stirred under nitrogen at room temperature. After ˜144 h, the reaction mixture was diluted with EtOAc (50 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (2×)(alumina, chloroform to 10% MeOH/CHCl3 gradient) to give the desired product as a light yellow oil (.0796 g, 78%); 1H NMR (400 MHz, DMSO-d6) δ1.18-1.40 (m, 6H), 1.63-1.71 (m, 2H), 2.50 (t, J=6.4 Hz, 2H), 3.82 (s, 3H), 4.21 (t, J=6.6 Hz, 2H), 7.01-7.06 (m, 2H), 7.87-7.92 (m, 2H); IR (KBr) 3410 (broad), 2940, 1710, 1605, 1510, 1260 cm−1; mass spectrum[(+)ESI], m/z 252 (M+H)+.

後処理

  1. dry with materialdried over Na2SO4
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vac
  4. customdried
  5. customThe residue was purified by flash chromatography (2×)(alumina, chloroform to 10% MeOH/CHCl3 gradient)

出典と根拠

ORDレコード
ord-177677bf5cbb4a2a8dd52ccdd3f0c629
出典データセット
uspto-grants-2001_04
特許番号
US06214877B1

反応ノート

読み込み中…