Water → 9-Fluorenylmethyl carbamate

HRID 1261576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261576
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(O[C@H]1[C@@H:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21](OC)=[CH:22][CH:23]=2)NC[C@@H]1O)=O.C1C2C(CC3C[C:45](=[O:47])[NH:44]C3=O)C3C(=CC=CC=3)C=2C=CC=1.[OH2:48]>C(#N)C>[C:45](=[O:47])([O:48][CH2:16][CH:17]1[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:6]2[C:1]1=[CH:2][CH:3]=[CH:4][CH:5]=2)[NH2:44]

Komponenten

6

Edukt 4

HCID 962WaterHCID 996PhenolHCID 253602AnisomycinHCID 223234189-Fluorenylmethyl succinimide

Produkt 1

HCID 7363019-Fluorenylmethyl carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Phenol 21 in FIG. 40 was synthesized as follows. Anisomycin 19 (0.5 g 1.88 mmol) was suspended in 15 mL of acetonitrile. 9-Fluorenylmethyl succinimide (0.762 g 2.26 mmol) was added to the suspension. Upon addition, all solid dissolved. After stirring for 16 hours at room temperature, water was added to the reaction solution, and it was extracted with ethyl acetate. The organics were combined and dried over sodium sulfate. After filtration and concentration, purification was accomplished by column chromatography using 3:1 hexanes:ethyl acetate as the mobile phase. This gave 9-fluorenylmethyl carbamate 20 as foam in quantitative yields (0.916 g).

Aufarbeitung

  1. additionUpon addition
  2. dissolutionall solid dissolved
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and concentration, purification

Quellen und Nachweise

ORD-Eintrag
ord-201322ecdd9d40a7bbb350d182b4424e
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470990B2

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