Methanol → HCID 4416748, compound

HRID 403636Notes

Reaction equation

HRID 403636 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2.Cl.[NH2:21][OH:22].C[O-].[Na+].CO.C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C.O>[CH:17]1[C:18]2[N:6]([CH2:5][CH2:4][C:3]([NH:21][OH:22])=[O:2])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

9

Reactant 5

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 105869809H-Carbazole-9-propanoic acid, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 4416748HCID 4416748, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Carbazol-9-yl-propionic acid methyl ester (22) (0.50 g, 1.97 mmol) and hydroxylamine hydrochloride (0.82 g, 12 mmol) were placed under argon and dissolved in DMF (8 mL). To it was added a 25% sodium methoxide solution in methanol (3.4 g, 16 mmol) which resulted in immediate precipitation of a white solid. The reaction was stirred for 24 h at room temperature after which was taken up in ethyl acetate (20 mL), water (10 mL) and of saturated aqueous NaHCO3 (10 mL). The organic layer was isolated and the aqueous layer was further extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo. The crude extract was purified by HPLC to yield the title compound (234 mg, 47%) as a white solid. 1H NMR (400 MHz, DMSO): δ 10.46 (s, 1H), 8.75 (s, 1H), 8.14 (d, 2H, J=7.7 Hz), 7.60 (d, 2H, J=8.0 Hz), 7.45 (t, 2H, J=7.2 Hz), 7.20 (t, 2H, J=7.6 Hz), 4.61 (t, 2H, J=6.8 Hz), 2.48 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 169.2, 140.2, 126.2, 122.6, 120.6, 119.3, 109.8, 39.3, 32.3. ESI-MS (m/z): [M+H]+ 254.1. Analytical HPLC: Purity=97%, tR=5.62 min, Method A.

Workup

  1. customresulted in immediate precipitation of a white solid
  2. customThe organic layer was isolated
  3. extractionthe aqueous layer was further extracted with ethyl acetate (2×20 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. extractionThe crude extract
  8. customwas purified by HPLC

Sources & evidence

ORD record
ord-621c17f044024e1098044d1dceaafdad
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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