4-(Heptyloxy)benzoyl chloride → 4-((4-Nitrobenzamido)methyl)phenyl 4-(heptyloxy)benzoate

HRID 923528ノート

反応式

HRID 923528 の反応式
[OH:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:21]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[CH2:21]([O:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8](=[O:18])[C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=3)=[CH:19][CH:20]=2)=[O:34])=[CH:36][CH:37]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

参加物

4

反応物 2

HCID 27241824-(Heptyloxy)benzoyl chlorideHCID 12714523N-(4-hydroxybenzyl)-4-nitrobenzamide

生成物 1

HCID 892530414-((4-Nitrobenzamido)methyl)phenyl 4-(heptyloxy)benzoate収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Prepared using General Procedure 2: To a stirring solution of N-(4-hydroxybenzyl)-4-nitrobenzamide INT-1 (647 mg, 2.38 mmol) in DCM (10 mL) at 0° C. was added TEA (1.03 mL, 7.13 mmol) followed by 4-(heptyloxy)benzoyl chloride (12.4 mL, 2.85 mmol). The suspension was sonicated until clear then diluted with DCM (50 mL) and washed with NaHCO3 (20 mL). The organic layer was concentrated and purified by chromatography (EA/hexanes) to provide 857 mg (73%) of 4-((4-nitrobenzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-2. LCMS-ESI (m/z) calculated for C28H30N2O6: 490; found 491 [M+H]+, tR=3.41 min (Method 5).

後処理

  1. customPrepared
  2. customThe suspension was sonicated until clear
  3. washwashed with NaHCO3 (20 mL)
  4. concentrationThe organic layer was concentrated
  5. custompurified by chromatography (EA/hexanes)

出典と根拠

ORDレコード
ord-d14024c373c8414da7ec56315486a940
出典データセット
uspto-grants-2016_03
特許番号
US09278910B2

反応ノート

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