2,2-Dimethoxypropane → HCID 68277206, Verbindung

HRID 406518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406518
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:27])[NH:17][C@@H:18]3[CH2:22][C@H:21]([CH2:23][OH:24])[C@@H:20]([OH:25])[C@H:19]3[OH:26])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CO[C:30](OC)([CH3:32])[CH3:31].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)(Cl)Cl.CO.C(O)(=O)C>CC(C)=O>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:27])[NH:17][C@H:18]3[C@H:19]4[C@H:20]([O:25][C:30]([CH3:32])([CH3:31])[O:26]4)[C@@H:21]([CH2:23][OH:24])[CH2:22]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 21866353chloroform methanol HOAcHCID 71623617((1R,2S,3R,4R)-2,3-Dihydroxy-4-hydroxymethyl-cyclopentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Produkt 1

HCID 68277206HCID 68277206, VerbindungAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

((1R,2S,3R,4R)-2,3-Dihydroxy-4-hydroxymethyl-cyclopentyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (115 g, 310 mmol), 2,2-dimethoxypropane (360 ml, 3.10 mol) and p-toluenesulfonic acid monohydrate (118 g, 620 mmol) were dissolved in dry acetone (2.00 l). The mixture was stirred for 3.5 h at room temperature to the complete consumption of the starting material according to TLC (Silicagel Merck 60, chloroform/methanol/acetic acid 9:1+0.1% v/v/v). The resulting suspension was stirred 15 min at 0° C. and the precipitate was filtered off and washed with cold acetone. The obtained brown solid was suspended again in diethylether (800 ml) and stirred for 20 min, filtered off, washed with diethylether (400 ml) and dried 8 h under reduced pressure giving 116 g (91%) of the title compound.

Aufarbeitung

  1. stirringThe resulting suspension was stirred 15 min at 0° C.
  2. filtrationthe precipitate was filtered off
  3. washwashed with cold acetone
  4. stirringstirred for 20 min
  5. filtrationfiltered off
  6. washwashed with diethylether (400 ml)
  7. customdried 8 h under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d86adc5ea92a43c88d508e702a560f10
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754111B2

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