Methyl 4-aminobenzoate → Methyl 4-({[4-(1-adamantyl)phenoxy]acetyl}amino)benzoate

HRID 1945371노트

반응식

HRID 1945371 반응식
[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1.Cl.C(N=C=N)C.OS1C2C=CC=CC=2N=C1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:22][O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:17](=[O:18])[CH2:16][O:15][C:14]2[CH:13]=[CH:12][C:11]([C:1]34[CH2:10][CH:5]5[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]5)[CH2:8]3)[CH2:2]4)=[CH:21][CH:20]=2)=[CH:27][CH:26]=1

참가 물질

7

반응물 5

HCID 12082Methyl 4-aminobenzoateHCID 81531DiisopropylethylamineHCID 625381PMID26882240-Compound-8HCID 21883477Ethylcarbodiimide hydrochlorideHCID 178527226HCID 178527226, 화합물

생성물 1

HCID 3470321Methyl 4-({[4-(1-adamantyl)phenoxy]acetyl}amino)benzoate수율 51.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of [4-(1-adamantyl)phenoxy]acetic acid (143.2 mg, 0.5 mmol), 4-aminobenzoic acid methyl ester (113.4 mg, 0.5 mmol), N-3-dimethylaminopropyl)-N′-ethyl carbodiimide HCl (EDC) (143.8 mg, 0.75 mmol) and 1-hydroxybenzothiazole (HOBt) (101.4 mg, 0.75 mmol) in DMF (6 mL) was added N,N-diisopropylethylamine, redistilled (DIPEA) (97.0 mg, 0.13 mL, 0.75 mmol). The mixture was stirred overnight, and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1) to give 4-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (108.3 mg, 51.7% yield).

후처리

  1. distillationredistilled (DIPEA) (97.0 mg, 0.13 mL, 0.75 mmol)
  2. custompartitioned between ethyl acetate and 10% HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1)

출처 및 근거

ORD 기록
ord-5bb3175da738406fa5654c450b5e71e7
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394799B2

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