Water → 9-Fluorenylmethyl carbamate

HRID 496961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496961
[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-8f1f127110d14f27b8b6d2ef0c764dfe
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06947845B2

Notizen zur Reaktion

Wird geladen…