N-Methyl-D-glucamine → 5-{[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]carbonyl}-2-hydroxybenzoic acid N-methyl-D-glucamine

HRID 551921Notes

Reaction equation

HRID 551921 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:38]=[CH:37][C:16]([CH2:17][N:18]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:19]([C:21]3[CH:22]=[CH:23][C:24]([OH:30])=[C:25]([CH:29]=3)[C:26]([OH:28])=[O:27])=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:39][NH:40][CH2:41][C@@H:42]([C@H:44]([C@@H:46]([C@@H:48]([CH2:50][OH:51])[OH:49])[OH:47])[OH:45])[OH:43]>CO.O>[CH3:39][NH:40][CH2:41][C@@H:42]([C@H:44]([C@@H:46]([C@@H:48]([CH2:50][OH:51])[OH:49])[OH:47])[OH:45])[OH:43].[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:38]=[CH:37][C:16]([CH2:17][N:18]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:19]([C:21]3[CH:22]=[CH:23][C:24]([OH:30])=[C:25]([CH:29]=3)[C:26]([OH:28])=[O:27])=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8567N-Methyl-D-glucamineHCID 575545135-{[{4-[(4-Butylphenyl)ethynyl]benzyl}(hexyl)amino]carbonyl)-2-hydroxybenzoic acid

Product 1

HCID 671714925-{[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]carbonyl}-2-hydroxybenzoic acid N-methyl-D-glucamineYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 5-{[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]carbonyl}-2-hydroxybenzoic acid (91 mg, 98 mmol) in MeOH (2 mL) was added a solution of N-methyl-D-glucamine (35 mg, 0.18 mmol) in water (2 mL). Water (20 mL) was added and the resulting solution was lyophilized to give 103 mg of the title compound as a white powder. HPLC, Rt: 5.73 min (purity: 99.6%). LC/MS, M+(ESI): 512.2, M−(ESI). 510.2. 1H NMR (CD3OD) δ: 0.84 (m, 3H), 0.94 (t, J=7.3 Hz, 3H), 2.28-1.40 (m, 8H), 1.60 (m, 4H), 2.62 (t, J=7.7 Hz, 2H), 2.69 (s, 3H), 3.15 (d, J=6.0 Hz, 2H), 3.31 (m, 2H), 3.63-3.83 (m, 5H), 4.03 (m, 1H), 4.72 (m, 2H), 6.86 (d, J=8.3 Hz, 1H), 7.18 (d, J=8.3 Hz 2H), 7.19 (m, 1H), 7.40 (d, J=7.9 Hz, 4H), 7.48 (d, J=7.9 Hz, 2H), 7.99 (d, J=2.3 Hz, 1H). M+(ESI): 512.2, M−(ESI): 510.2.

Sources & evidence

ORD record
ord-c52cb442c06d46b2b33740ecd33ceb37
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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