Sodium Iodide → HCID 49869900、化合物

HRID 57213

反応式

HRID 57213 の反応式
[CH2:1]([N:8]([CH3:15])[C:9](=[O:14])[O:10][CH:11](Cl)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:30][C:31]1[O:35][C:34]([C:36]([OH:38])=[O:37])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].O.O.O.O.O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[Na+]>CN(C)C=O>[CH2:16]([O:30][C:31]1[O:35][C:34]([C:36]([O:38][CH:11]([O:10][C:9](=[O:14])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:15])[CH3:12])=[O:37])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 1151755-(Tetradecyloxy)-2-furoic acidHCID 66869455HCID 66869455、化合物HCID 86669148HCID 86669148、化合物

生成物 1

HCID 49869900HCID 49869900、化合物収率 43%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

The above prepared 1-chloroethyl benzyl(methyl)carbamate was dissolved in N,N-dimethylformamide (5 mL) and then 5-(tetradecyloxy)furan-2-carboxylic acid (0.180 g, 0.544 mmol), tetrabutylammonium hydroxide pentahydrate (0.209 g, 0.60 mmol), and sodium iodide (˜15 mg) were added to the reaction vessel. The resulting suspension was heated to 60° C. with stirring for 14 hrs. HPLC analysis of the reaction solution indicated that all of the starting material had been converted to a product of lower polarity. The reaction was then quenched with brine (5 mL), water (5 mL) and EtOAc (70 mL). The organic phase was washed successively with water (30 mL) and brine (30 mL) and then dried and concentrated. The resulting crude material was purified by flash chromatography eluting with EtOAc in hexanes, 5-20% to yield 0.120 g (43%) of the title compound as a slightly brown oil. 1H NMR (300 MHz, CDCl3) δ: 7.15-7.40 (m, 6H), 7.05 (p, 1H), 5.30 (d, 1H), 4.40-4.60 (m, 2H), 4.10 (t, 2H), 2.85 (d, 3H) 1.7-1.9 (m, 2H), 1.79 (p, 2H), 1.55-1.62 (m, 3H), 1.18-1.50 (m, 22H), 0.89 (t, 3H).

後処理

  1. customThe reaction was then quenched with brine (5 mL), water (5 mL) and EtOAc (70 mL)
  2. washThe organic phase was washed successively with water (30 mL) and brine (30 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting crude material was purified by flash chromatography
  6. washeluting with EtOAc in hexanes, 5-20%

出典と根拠

ORDレコード
ord-8bfc49ee52d24267bb244325ca5c1fa3
出典データセット
uspto-grants-2016_09
特許番号
US09434718B2

関連ノート

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