Methanol → tert-butyl 2-(N-(4-chlorobenzyl)piperazine-1-carboxamido)ethylcarbamate

HRID 80987

Reaktionsgleichung

Reaktionsgleichung von HRID 80987
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C:12]([N:14]1[CH2:19][CH2:18][N:17](C(OCC2C=CC=CC=2)=O)[CH2:16][CH2:15]1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].CO.O.[OH-].[K+].CO>O>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][N:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:12]([N:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[O:13])=[CH:36][CH:35]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 53416583Benzyl 4-({2-[(tert-butoxycarbonyl)amino]ethyl}[(4-chlorophenyl)methyl]carbamoyl)piperazine-1-carboxylateHCID 86591755KOH MeOH Water

Produkt 1

HCID 67135341tert-butyl 2-(N-(4-chlorobenzyl)piperazine-1-carboxamido)ethylcarbamateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of benzyl 4-((2-(tert-butoxycarbonylamino)ethyl)(4-chlorobenzyl)carbamoyl)piperazine-1-carboxylate (200 mg, 0.38 mmol) in a KOH/MeOH/H2O (10 mL; prepared as a stock solution using 10 g KOH, 50 mL MeOH and 25 mL H2O) solution of was stirred for 2 hours at 80° C. The reaction was extracted with EtOAc, dried over NaSO4 and concentrated under reduced pressure to yield tert-butyl 2-(N-(4-chlorobenzyl)piperazine-1-carboxamido)ethylcarbamate (132 mg, 89%). MS (ESI) m/e (M+H+) 397.

Aufarbeitung

  1. customprepared as a stock solution
  2. extractionThe reaction was extracted with EtOAc
  3. dry with materialdried over NaSO4
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-12cf4848e62f42c6bb7abe563c366f7f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846683B2

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