Diisopropylethylamine → Methyl 3-{[(5-methoxy-2,5-dioxopentyl)amino]carbonyl}benzoate

HRID 14089

反応式

HRID 14089 の反応式
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[CH:3]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:48][O:49][C:50](=[O:57])[CH2:51][CH2:52][C:53]([CH2:55][NH2:56])=[O:54]>C(Cl)Cl.CN(C=O)C>[CH3:48][O:49][C:50](=[O:57])[CH2:51][CH2:52][C:53](=[O:54])[CH2:55][NH:56][C:5]([C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][CH:8]=1)[C:1]([O:12][CH3:13])=[O:11])=[O:7]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 157921Methyl Aminolevulinate HydrochlorideHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 21086156Methyl 3-{[(5-methoxy-2,5-dioxopentyl)amino]carbonyl}benzoate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

Methyl hydrogen isophthalate (1.8 g, 10.2 mmol) is dissolved in methylene chloride (10 mL) and DMF (10 mL), and diisopropylethylamine (4.4 mL, 25.5 mmol), HATU (4.6 g, 12.2 mmol), and 5-aminolevulinic acid methyl ester hydrochloride (2 g, 11.2 mmol) are added. The reaction stirred at room temperature 1 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 4% methanol/chloroform) provides the title compound. ESI MS m/z 306.1 [M−H]−.

後処理

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

出典と根拠

ORDレコード
ord-6c497afda407464e814092529b9f0fb5
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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