Nitrogen → HCID 10926410, compound

HRID 19962Notes

Reaction equation

HRID 19962 reaction equation
[OH:1][CH:2]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:3]([NH:5][C@@H:6]([CH2:19][CH2:20][CH2:21][CH3:22])/[CH:7]=[CH:8]/[C:9]([O:11]CC1C=CC=CC=1)=[O:10])=[O:4].N#N>CCO.[Pd]>[OH:1][CH:2]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:3]([NH:5][C@@H:6]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:4]

Participants

5

Reactant 2

HCID 947NitrogenHCID 10928405Benzyl(E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate

Product 1

HCID 10926410HCID 10926410, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl (E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate (0.445 g, 1 mmol) in EtOH (2.5 mL), through which N2 had been passed for 5 min, 10% Pd/C catalyst (0.042 g) was added. The reaction mixture was stirred under H2 for 5 h at room temperature. The catalyst was removed by filtration through a pad of Celite and the filtrate was evaporated under reduced pressure. The product was purified by column chromatography (CHCl3/MeOH 9/1). Yield 0.28 g (70%); mp 53-55° C.; [α]D−2.4 (c 0.75 CHCl3); 1H NMR δ 6.82 (1H, m, NH), 4.18 (1H, m, CHNH), 3.91 (1H, m, CHOH), 2.39 (2H, t, J=6.3 Hz, CH2COOH), 1.95-1.12 (26H, m, 13×CH2), 0.88 (3H, t, J=6.0 Hz, CH3); Anal. Calcd. for C20H39NO4: C, 67.19; H, 10.99; N, 3.92. Found: C, 67.05; H, 11.18; N, 3.63.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe product was purified by column chromatography (CHCl3/MeOH 9/1)

Sources & evidence

ORD record
ord-7a8357ff9a39405db8f31c9c82e114da
Source dataset
uspto-grants-2010_06
Patent number
US07745489B2

Reaction notes

Loading…