Imidazole → 2-hydroxy-N-(2-((4Z,7Z,10Z,13Z,16Z,19Z)-N-methyldocosa-4,7,10,13,16,19-hexaenamido)ethyl)benzamide

HRID 85373

반응식

HRID 85373 반응식
[NH2:1][CH2:2][CH2:3][N:4]([CH3:28])[C:5](=[O:27])[CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH3:26].[OH:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33].N1C=CN=C1.C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[OH:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([NH:1][CH2:2][CH2:3][N:4]([CH3:28])[C:5](=[O:27])[CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH3:26])=[O:33]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 10868DicyclohexylcarbodiimideHCID 74041Salicyloyl chlorideHCID 59193341(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-aminoethyl)-N-methyldocosa-4,7,10,13,16,19-hexaenamide

생성물 1

HCID 591933012-hydroxy-N-(2-((4Z,7Z,10Z,13Z,16Z,19Z)-N-methyldocosa-4,7,10,13,16,19-hexaenamido)ethyl)benzamide수율 73.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-aminoethyl)-N-methyldocosa-4,7,10,13,16,19-hexaenamide (104 mg, 0.27 mmol), 2-hydroxybenzoyl chloride (37 mg, 0.27 mmol) and imidazole (19 mg, 0.27 mmol) in EtOAc (4 mL) at 0° C. was added dropwise a solution of DCC (0.57 g, 0.27 mmol) in EtOAc (4 mL). The mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel, eluting with EtOAc-PE (1:3) to afford 2-hydroxy-N-(2-((4Z,7Z,10Z,13Z,16Z,19Z)—N-methyldocosa-4,7,10,13,16,19-hexaenamido)-ethyl)-benzamide (100 mg, 73%) as a colorless oil. Mass calculated for C32H44N2O3=504.70; found: [M+H]+=505.5.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by chromatography on silica gel
  4. washeluting with EtOAc-PE (1:3)

출처 및 근거

ORD 기록
ord-92226bb7292b4619b13279511c88b3aa
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846972B2

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