Hydrochloric Acid → HCID 53248105, compound

HRID 882675Notes

Reaction equation

HRID 882675 reaction equation
C(O[C:6]([NH:8][CH2:9][CH:10]([S:15]([OH:18])(=[O:17])=[O:16])[CH2:11][C:12]([OH:14])=[O:13])=[O:7])(C)(C)C.Cl.O1CCOCC1.C1(=O)[O:31][C:29](=[O:30])[CH:28]=[CH:27]1>CC(N(C)C)=O>[C:12]([CH2:11][CH:10]([S:15]([OH:18])(=[O:16])=[O:17])[CH2:9][NH:8][C:6](=[O:7])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30])([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 312751,4-DioxaneHCID 53248162HCID 53248162, compound

Product 1

HCID 53248105HCID 53248105, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

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.

Workup

  1. customevaporated
  2. customevaporated
  3. washeluted with water
  4. customcrystallized with EtOH/Hexane

Sources & evidence

ORD record
ord-dd47d1b2c9c34da483474007ec8960c1
Source dataset
uspto-grants-2012_08
Patent number
US08236319B2

Reaction notes

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