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

HRID 14089Notes

Reaction equation

HRID 14089 reaction equation
[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]

Participants

7

Reactant 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)

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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]−.

Workup

  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)

Sources & evidence

ORD record
ord-6c497afda407464e814092529b9f0fb5
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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