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Phenacyl bromide → N-tert-butoxycarbonyl-2-(4-phenacyloxyphenyl)glycin phenacyl ester

HRID 444424
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 444424
[CH2:1]([O:10][C:11](=[O:28])[CH:12]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[CH2:29](Br)[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:10][C:11](=[O:28])[CH:12]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:29][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:31])=[CH:25][CH:26]=1)[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 20559123N-tert-butoxycarbonyl-2-(4-hydroxyphenyl)glycine phenacyl ester

Produkt 1

HCID 20243679N-tert-butoxycarbonyl-2-(4-phenacyloxyphenyl)glycin phenacyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of N-tert-butoxycarbonyl-2-(4-hydroxyphenyl)glycine phenacyl ester prepared as above (3.56 g.), phenacyl bromide (1.84 g.) and potassium carbonate (1.28 g.) in an anhydrous acetone (71 ml.) was heated to reflux for 7 hours. The insoluble substances were filtered off and the filtrate was evaporated to dryness under reduced pressure. The residual oil was dissolved in chloroform, washed with water, dried over magnesium sulfate, and evaporated to dryness under reduced pressure. The residue was triturated with diisopropyl ether to give crystalline N-tert-butoxycarbonyl-2-(4-phenacyloxyphenyl)glycine phenacyl ester (4.12 g.), which was recrystallized from ethanol to give the pure material, mp 125° to 126.5° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. filtrationThe insoluble substances were filtered off
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. dissolutionThe residual oil was dissolved in chloroform
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness under reduced pressure
  9. customThe residue was triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f1238345f94141f9a9d61f085b2af688
Quelldatensatz
uspto-grants-1981_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04264498

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