Réaction #969857

ord-dd47d1b2c9c34da483474007ec8960c1

Équation de réaction

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
Rendement 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
Rendement 83.0%

Réactifs

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

Réactifs

Aucun

Solvants

CC(=O)N(C)C
DMA

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreevaporated
  2. 2
    Autreevaporated
  3. 3
    Lavageeluted with water
  4. 4
    Autrecrystallized with EtOH/Hexane

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08236319B2uspto-grants-2012_08