Sodium Hydroxide → 2-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol 2-hydroxyethanesulfonate

HRID 1761995

Reaktionsgleichung

Reaktionsgleichung von HRID 1761995
[CH3:1][S:2]([O:5][CH2:6][C:7]([NH:11][CH2:12][C:13]1[CH:14]=[C:15]2[C:24](=[C:25]3[C:30]=1[CH:29]=[CH:28][CH:27]=[CH:26]3)[CH:23]=[CH:22][C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]2=1)([CH3:10])[CH2:8][OH:9])(=[O:4])=[O:3].[OH-:31].[Na+].[CH3:33]O.O>>[CH:20]1[C:21]2[CH:22]=[CH:23][C:24]3[C:15](=[CH:14][C:13]([CH2:12][NH:11][C:7]([CH3:10])([CH2:6][OH:5])[CH2:8][OH:9])=[C:30]4[C:25]=3[CH:26]=[CH:27][CH:28]=[CH:29]4)[C:16]=2[CH:17]=[CH:18][CH:19]=1.[OH:31][CH2:33][CH2:1][S:2]([O-:5])(=[O:3])=[O:4]

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 22242641Methanol--water (1/1)HCID 540960872-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol methanesulfonate

Produkt 1

HCID 1317154222-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol 2-hydroxyethanesulfonateAusbeute 70,4 %

Versuchsvorschrift

2-((6-chrysenylmethyl)amino)-2-methyl-1,3-propanediol methanesulfonate (1C, 10.0 g, 26.63 mmol) was neutralized with 1N NaOH (30 mL) in CH3OH/H2O (200/800 mL) as in procedure 1D. The white solid which formed was filtered, washed successively with warm H2O (3×500 mL), CH3OH (200 mL), and abs. Et2O (2×500 mL), sucked semi-dry and then resuspended in CH3OH (500 mL). To this was added a 0.43M aqueous solution of 2-hydroxyethanesulfonic acid (30 mL). Slight warming gave a solution which was then filtered. The solvent was removed by rotary evaporation to give a wet white solid. This was triturated with dry Et2O, filtered, and recrystallized 3× from EtOH/Et2O to give 8.8 g (70.4%) of 2-((6-chrysenylmethyl)amino)-2-methyl-1,3-propanediol 2-hydroxyethanesulfonate, mp 212°-213°, (C, H, N, S).

Aufarbeitung

  1. customThe white solid which formed
  2. filtrationwas filtered
  3. washwashed successively with warm H2O (3×500 mL), CH3OH (200 mL), and abs
  4. additionTo this was added a 0.43M aqueous solution of 2-hydroxyethanesulfonic acid (30 mL)
  5. temperatureSlight warming
  6. customgave a solution which
  7. filtrationwas then filtered
  8. customThe solvent was removed by rotary evaporation
  9. customto give a wet white solid
  10. customThis was triturated with dry Et2O
  11. filtrationfiltered
  12. customrecrystallized 3× from EtOH/Et2O

Quellen und Nachweise

ORD-Eintrag
ord-8319c1b1b10a4798a5723e082b7f80df
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04829090

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