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

HRID 923528노트

반응식

HRID 923528 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d14024c373c8414da7ec56315486a940
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278910B2

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