1,5-Naphthalenedisulfonic acid → HCID 11355034, compound

HRID 2252104Notes

Reaction equation

HRID 2252104 reaction equation
[Si]([O:8][C@H:9]([C:43]1[CH:52]=[CH:51][C:50]([OH:53])=[C:49]2[C:44]=1[CH:45]=[CH:46][C:47](=[O:54])[NH:48]2)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([O:27][C:28](=[O:42])[NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:23][CH2:22]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:73]1([S:87]([OH:90])(=[O:89])=[O:88])[C:82]2[CH:81]=[CH:80][CH:79]=[C:78]([S:83]([OH:86])(=[O:85])=[O:84])[C:77]=2[CH:76]=[CH:75][CH:74]=1>C1COCC1.CO>[C:73]1([S:87]([OH:90])(=[O:89])=[O:88])[C:82]2[CH:81]=[CH:80][CH:79]=[C:78]([S:83]([OH:86])(=[O:85])=[O:84])[C:77]=2[CH:76]=[CH:75][CH:74]=1.[OH:8][C@H:9]([C:43]1[CH:52]=[CH:51][C:50]([OH:53])=[C:49]2[C:44]=1[CH:45]=[CH:46][C:47](=[O:54])[NH:48]2)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][CH:24]([O:27][C:28](=[O:42])[NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 66661,5-Naphthalenedisulfonic acidHCID 2724141Tetrabutylammonium FluorideHCID 66967735HCID 66967735, compound

Product 1

HCID 11355034HCID 11355034, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

To a 500-mL round-bottomed flask was added the crude biphenyl-2-yl-carbamic acid 1-{9-[(R)-2-(tert-butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]nonyl}piperidin-4-yl ester (16 g, 18.5 mmol) and THF (100 mL) and the resulting mixture was stirred until the compound dissolved (about 10 min). A 1M solution of tetrabutylammonium fluoride (37 μL, 37 mmol) in THF was added and the resulting mixture was stirred at 40° C. under nitrogen for 6 to 7 hours (>98% conversion by HPLC). The mixture was then cooled to 30° C., and a solution of naphthalene-1,5-disulfonic acid (4.26 g, 14.8 mmol, recrystallized from acetonitrile) in methanol (100 mL) was added. The reaction mixture was then stirred at 30° C. for 3 to 4 hours and then at room temperature for 2 hours. The resulting crystalline solid was then collected by filtration, washed with methanol (20 mL) and air dried to give the title compound as an off-white crystalline solid (8 g).

Workup

  1. dissolutiondissolved (about 10 min)
  2. stirringthe resulting mixture was stirred at 40° C. under nitrogen for 6 to 7 hours (>98% conversion by HPLC)
  3. stirringThe reaction mixture was then stirred at 30° C. for 3 to 4 hours
  4. filtrationThe resulting crystalline solid was then collected by filtration
  5. washwashed with methanol (20 mL) and air
  6. customdried

Sources & evidence

ORD record
ord-3b7119eddca54290bdde4a46da0c940f
Source dataset
uspto-grants-2008_01
Patent number
US07320990B2

Reaction notes

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