Reaktion #59810

ord-c9d0a650785e48d2b2c404f41e04eaa4

Reaktionsgleichung

COC(=O)c1cc(NC(=O)OC(C)(C)C)nn1CC(=O)OC(C)(C)C
5-tert-Butoxycarbonylamino-2-tert-butoxycarbonylmethyl-2H-pyrazole-3-carboxylic acid methyl ester
[Li+].[OH-]
lithium hydroxide
Cl
hydrochloric acid
→
CC(C)(C)OC(=O)Nc1cc(C(=O)O)n(CC(=O)O)n1
title product
Ausbeute 122.1%
CC(C)(C)OC(=O)Nc1cc(C(=O)O)n(CC(=O)O)n1
5-tert-Butoxycarbonylamino-2-carboxymethyl-2H-pyrazole-3-carboxylic acid
Ausbeute 122.1%

Edukte

COC(=O)c1cc(NC(=O)OC(C)(C)C)nn1CC(=O)OC(C)(C)C
5-tert-Butoxycarbonylamino-2-tert-butoxycarbonylmethyl-2H-pyrazole-3-carboxylic acid methyl ester
[Li+].[OH-]
lithium hydroxide
Cl
hydrochloric acid

Reagenzien

Keine

Lösungsmittel

C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionthe product extracted with dichloromethane
  2. 2
    TrocknenThe extract was dried over magnesium sulfate
  3. 3
    Filtrationfiltered
  4. 4
    Sonstigeevaporated

Vorschrift

To a solution of 5-tert-Butoxycarbonylamino-2-tert-butoxycarbonylmethyl-2H-pyrazole-3-carboxylic acid methyl ester (0.5 gm) dissolved in 25 ml of tetrahydrofuran was added 5 ml of 1M lithium hydroxide. After stirring the reaction mixture at 60 C for 2 hours, 1N hydrochloric acid was added and the product extracted with dichloromethane. The extract was dried over magnesium sulfate, filtered and evaporated to obtain 0.49 gm of title product. ESI M+1=286.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07425640B2uspto-grants-2008_09