Sulfuric Acid → 9H-Fluoren-9-ylmethyl 12,12-dimethyl-10-oxo-5,8,11-trioxa-2-azatridecanoate

HRID 2275467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275467
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]([OH:28])=[O:27])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:29][C:30](=[CH2:32])[CH3:31].OS(O)(=O)=O>ClCCl>[C:30]([O:27][C:26](=[O:28])[CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][NH:18][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17])([CH3:32])([CH3:31])[CH3:29]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 27560922-(2-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)ethoxy)acetic acid

Produkt 1

HCID 675195109H-Fluoren-9-ylmethyl 12,12-dimethyl-10-oxo-5,8,11-trioxa-2-azatridecanoateAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 150 mg (0.389 mmol) of 8-(9-Fluorenylmethoxycarbonylamino)-3,6-dioxaoctanoic acid, 546 mg (9.73 mmol) isobutylene, and 4.3 μL of 95-98% H2SO4 was stirred at r.t. for 3 days. For workup the reaction solution was diluted with dichloromethane and washed with sat. bicarbonate solution. After drying over sodium sulfate the solvent was removed and the residue obtained purified by chromatography on silica gel with a cHex/EtOAc gradient providing 145 mg (84.4%) of the title compound. ESI MS: 464.12 [M+Na]+.

Aufarbeitung

  1. washwashed with sat. bicarbonate solution
  2. dry with materialAfter drying over sodium sulfate the solvent
  3. customwas removed
  4. customthe residue obtained
  5. custompurified by chromatography on silica gel with a cHex/EtOAc gradient

Quellen und Nachweise

ORD-Eintrag
ord-d53d78ee4b37400e850abc2db39920ff
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09127044B2

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