Reaktion #2001631

ord-c510a1581fed4778b5e0853297d37da3

Reaktionsgleichung

CC(C)(C)OC(=O)NCC(CC(=O)O)S(=O)(=O)O
4-(Tert-butoxycarbonylamino)-3-sulfobutanoic acid
Cl
HCl
C1COCCO1
Dioxane
O=C1C=CC(=O)O1
maleic anhydride
→
O=C(O)/C=C\C(=O)NCC(CC(=O)O)S(=O)(=O)O
title compound
Ausbeute 83.0%
O=C(O)/C=C\C(=O)NCC(CC(=O)O)S(=O)(=O)O
(Z)-4-(3-carboxy-2-sulfopropylamino)-4-oxobut-2-enoic acid
Ausbeute 83.0%

Edukte

CC(C)(C)OC(=O)NCC(CC(=O)O)S(=O)(=O)O
4-(Tert-butoxycarbonylamino)-3-sulfobutanoic acid
Cl
HCl
C1COCCO1
Dioxane
O=C1C=CC(=O)O1
maleic anhydride

Reagenzien

Keine

Lösungsmittel

CC(=O)N(C)C
DMA

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeevaporated
  2. 2
    Sonstigeevaporated
  3. 3
    Wascheneluted with water
  4. 4
    Sonstigecrystallized with EtOH/Hexane

Vorschrift

4-(Tert-butoxycarbonylamino)-3-sulfobutanoic acid (321 mg, 1.13 mmol) was stirred in the mixture of HCl (conc)/Dioxane (1:4, 15 ml) for 30 min, evaporated and coevaporated with EtOH/Toluene (1:1, 4×20 ml) to dryness. To the dryness material was added maleic anhydride (121 mg, 1.23 mmol) and DMA (20 ml) and the mixture was stirred overnight, evaporated and run through C-18 column eluted with water and crystallized with EtOH/Hexane to afford 263 mg (83%) of the title compound. ESI MS 279.8 (M−H). The NMR data are the same through the route with 4-azido-3-sulfobutanoic acid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08613930B2uspto-grants-2013_12