Methoxyacetic Acid → HCID 67090436, compound

HRID 2378736Notes

Reaction equation

HRID 2378736 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.Cl.Cl.[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](/[CH:18]=[CH:19]/[C:20]2[CH:33]=[CH:32][C:23]([C:24]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[O:25])=[C:22]([CH3:34])[CH:21]=2)=[N:10]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][C:4]([N:29]1[CH2:30][CH2:31][N:26]([C:24](=[O:25])[C:23]2[CH:32]=[CH:33][C:20](/[CH:19]=[CH:18]/[C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[NH:9][N:10]=3)=[CH:21][C:22]=2[CH3:34])[CH2:27][CH2:28]1)=[O:6]

Participants

8

Reactant 5

HCID 12251Methoxyacetic AcidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67089898HCID 67089898, compound

Product 1

HCID 67090436HCID 67090436, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methoxyacetic acid (0.019 mL, 0.24 mmol) in THF (5.0 mL) was added with Compound 95 (0.10 g, 0.29 mmol), 1-hydroxybenzotriazole monohydrate (52 mg, 0.337 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (69 mg, 0.36 mmol), followed by stirring at 60° C. for 1 hour. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution (4.0 mL) and was extracted. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/1), and the product was added with ethyl acetate, then precipitate was collected by filtration to obtain Compound 100 (39 mg, 39%).

Workup

  1. extractionwas extracted
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/1)
  4. additionthe product was added with ethyl acetate
  5. filtrationprecipitate was collected by filtration

Sources & evidence

ORD record
ord-2faf078d75134c2192477398c5e8f505
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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