HCID 19692717, compound → HCID 19027944, compound

HRID 1780784Notes

Reaction equation

HRID 1780784 reaction equation
[C:1]([CH2:4]/[CH:5]=[CH:6]/[C:7]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:11][CH:10]=[C:9]([CH2:30][OH:31])[N:8]=1)([OH:3])=[O:2]>CO.C(Cl)Cl>[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[CH:11][CH:10]=[C:9]([CH2:30][OH:31])[N:8]=1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 19692717HCID 19692717, compound

Product 1

HCID 19027944HCID 19027944, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-(E-2-Carboxymethyl-ethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-hydroxymethylpyridine (300 mg, 0.702 mmol) was dissolved in MeOH (3 mL) and treated with 5% Pd--C catalyst (30 mg). The reaction was stirred under an atmosphere of H2 (balloon pressure) for 5 hours. The reaction was diluted with CH2Cl2, and filtered through Celite, and concentrated. Purification by flash column chromatography (silica, EtOAc:CH2Cl2 :hexane, 25:50:25) gave a pale yellow oil: 1H NMR (250 MHz, CDCl3) δ 7.09 (m, 4H, phenyl, pyridyl), 6.80 (d, J=8.6 Hz, 2H, phenyl), 4.62 (s, 2H, CH2), 3.93 (t, J=6.5 Hz, 2H, OCH2), 3.77 (s, 3H, OCH3), 3.68 (s, 3H, methyl ester), 3.16 (dd, J=7.3, 7.2 Hz, 2H, CH2), 2.77 (dd, J=7.3, 7.2 Hz, 2H, CH2), 2.54 (t, J=7.6 Hz, 2H, benzylic), 1.79 (m, 2H, CH2), 1.57 (m, 2H, CH2), 1.44 (m, 2H, CH2), 1.34 (m, 6H, aliphatic); MS (CI): 430.2 (M+H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. customPurification by flash column chromatography (silica, EtOAc:CH2Cl2 :hexane, 25:50:25)
  4. customgave a pale yellow oil

Sources & evidence

ORD record
ord-e195cd22266641658c299517b6bb6306
Source dataset
uspto-grants-1997_05
Patent number
US05631262

Reaction notes

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