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

HRID 551892Notes

Reaction equation

HRID 551892 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:36]=[CH:35][C:16]([CH2:17][N:18]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:19]3[CH:20]=[CH:21][C:22]([OH:28])=[C:23]([CH:27]=3)[C:24]([OH:26])=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C1COCC1.[CH3:42][NH:43][CH2:44][C@@H:45]([C@H:47]([C@@H:49]([C@@H:51]([CH2:53][OH:54])[OH:52])[OH:50])[OH:48])[OH:46]>O>[CH3:42][NH:43][CH2:44][C@@H:45]([C@H:47]([C@@H:49]([C@@H:51]([CH2:53][OH:54])[OH:52])[OH:50])[OH:48])[OH:46].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:36]=[CH:35][C:16]([CH2:17][N:18]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:19]3[CH:20]=[CH:21][C:22]([OH:28])=[C:23]([CH:27]=3)[C:24]([OH:26])=[O:25])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8567N-Methyl-D-glucamineHCID 114972825-((4-((4-Butylphenyl)ethynyl)benzyl)(hexyl)amino)-2-hydroxybenzoic acid

Product 1

HCID 115203585-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-hydroxybenzoic acid N-methyl-D-glucamineYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of the 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-hydroxybenzoic acid (1650 mg, 3.41 mmol) in freshly distilled THF (20 mL) was added a solution of N-methyl-D-glucamine (666 mg) in water (4 mL). Water (200 mL) was added and the resulting solution was lyophilized to give 1.93 g (81%) of the title compound as a pale yellow powder. HPLC, Rt: 4.8 min (purity: 98.8%). LC/MS, M+(ESI): 484.0, M−(ESI): 482.0.

Sources & evidence

ORD record
ord-e6bcb7b2254c4597aec88fe455bf6890
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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