Triethylamine → Benzoic acid N'-(2-9H-fluoren-9-yl-acetyl)-N'-isopropyl-hydrazide

HRID 1724149

반응식

HRID 1724149 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][C:15](O)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:18]([NH:21][NH:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:20])[CH3:19].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH:1]1[C:13]2[CH:12]([CH2:14][C:15]([N:21]([CH:18]([CH3:20])[CH3:19])[NH:22][C:23](=[O:30])[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 188691-Benzoyl-2-isopropylhydrazineHCID 757711-HydroxybenzotriazoleHCID 94852Fluorene-9-acetic acid

생성물 1

HCID 57560117Benzoic acid N'-(2-9H-fluoren-9-yl-acetyl)-N'-isopropyl-hydrazide수율 40.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 9-fluoreneacetic acid (126 mg, 0.56 mmoles) and benzoic acid N′-isopropyl-hydrazide (100 mg, 0.56 mmoles) in DMF (5 mL) was treated with triethylamine (0.23 mL, 1.68 mmol), HOBT (91 mg, 0.67 mmoles) and EDCI (129 mg, 0.67 mmol) at room temperature for 72 h. The reaction mixture was partitioned between water and dichloromethane. The organic layer was washed with water and brine, then dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 10-30% ethyl acetate/hexanes gradient to afford the product as a solid (87 mg, 40%). LC-MS m/e 385.19 (M+H+)

후처리

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 10-30% ethyl acetate/hexanes gradient

출처 및 근거

ORD 기록
ord-3d7adb47e45b4550bc5045491a132aa7
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485752B2

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