N-Methylbutylamine → Methyl 3-{[butyl(methyl)amino]carbonyl)-5-iodobenzoate

HRID 14297

반응식

HRID 14297 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=N[C:34]2[CH:35]=[CH:36][CH:37]=[N:38][C:33]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CNCCCC>CN(C=O)C>[CH2:37]([N:38]([CH3:33])[C:5]([C:4]1[CH:8]=[C:9]([CH:10]=[C:2]([I:1])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:7])[CH2:36][CH2:35][CH3:34]

참가 물질

6

반응물 4

HCID 8068N-MethylbutylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acid

생성물 1

HCID 21086165Methyl 3-{[butyl(methyl)amino]carbonyl)-5-iodobenzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-Iodo-5-(methoxycarbonyl)benzoic acid (1 g, 3.3 mmol) is dissolved in DMF (10 mL), and diisopropylethylamine (1.7 mL, 9.8 mmol), HATU (1.5 g, 3.9 mmol), and N-methylbutylamine (581 μL, 4.9 mmol) are added. The reaction stirred at room temperature 2 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 40% ethyl acetate/hexane) provides the title compound. ESI MS m/z 376.1 [M+H]+.

후처리

  1. customThe reaction is partitioned between ethyl acetate and water
  2. washThe organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica, 40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-8da84dc1edd148bab8666c6537bcb486
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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