Lipoic acid → HCID 11698149, compound

HRID 969290Notes

Reaction equation

HRID 969290 reaction equation
[CH2:1]([N:3]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH2:10])[CH3:2].[CH2:20]1[C@@H:24]([CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])[S:23][S:22][CH2:21]1>>[CH2:1]([N:3]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[CH2:20][CH2:21][S:22][S:23]1)[CH3:2]

Participants

3

Reactant 2

HCID 6112Lipoic acidHCID 44598011N1-ethyl-N1-(2-methoxy-benzyl)-hexane-1,6-diamine

Product 1

HCID 11698149HCID 11698149, compoundYield 43%

Procedure

It was synthesized from N1-ethyl-N1-(2-methoxy-benzyl)-hexane-1,6-diamine (patent application PCT/IT03/0227) (300 mg, 1.13 mmol) and lipoic acid (350 mg, 1.70 mmol) following the procedure described for 17, and purified by gravity column. Elution with a gradient of mobile phase petroleum ether/toluene/CH2Cl2/EtOH/aqueous 30% ammonia solution (7:2:1:1:0.05 to 7:1:1:1:0.5) afforded 18 as a waxy solid: 43% yield, 1H NMR (200 MHz, CDCl3) δ 7.42-7.48 (m, 1H); 7.18-7.26 (m, 1H), 6.85-6.99 (m, 2H), 5.43 (br t, 1H, exchangeable with D2O), 3.84 (s, 3H), 3.53-3.64 (m, 1H+s, 2H), 3.08-3.27 (m, 4H), 2.43-2.57 (m, 5H), 2.17 (t, J=7.4 Hz, 2H), 1.82-2.00 (m, 1H), 1.29-1.73 (m, 14H), 1.07 (t, J=7.0 Hz, 3H); MS (ESI+) m/z 453 (M+H)+. Anal. Calculated for C24H40N2O2S2: C, 63.67; H, 8.91; N, 6.19. Found: C, 63.79; H, 8.93, N, 6.17.

Workup

  1. custompurified by gravity column
  2. washElution with a gradient of mobile phase petroleum ether/toluene/CH2Cl2/EtOH/aqueous 30% ammonia solution (7:2:1:1:0.05 to 7:1:1:1:0.5)

Sources & evidence

ORD record
ord-54b3e174b7f2476fb542e78fdc0ec537
Source dataset
uspto-grants-2007_12
Patent number
US07307083B2

Reaction notes

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