Methanesulfonic Acid → HCID 86641129, compound

HRID 2191060Notes

Reaction equation

HRID 2191060 reaction equation
[N:1]([C:4]1([CH2:19][OH:20])[O:8][CH:7]([N:9]2[CH:14]=[CH:13][C:12](=[O:15])[NH:11][C:10]2=[O:16])[CH:6]([OH:17])[CH:5]1[OH:18])=[N+:2]=[N-:3].CO[C:23](OC)([CH3:25])[CH3:24].S(O)(C)(=O)=O.C(N(CC)CC)C>CC(C)=O>[N:1]([C:4]1([CH2:19][OH:20])[CH:5]2[O:18][C:23]([CH3:25])([CH3:24])[O:17][CH:6]2[CH:7]([N:9]2[CH:14]=[CH:13][C:12](=[O:15])[NH:11][C:10]2=[O:16])[O:8]1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 64952,2-DimethoxypropaneHCID 8471TriethylamineHCID 22593591HCID 22593591, compound

Product 1

HCID 86641129HCID 86641129, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 48.2 (1.81 g, 6.35 mmol) was dissolved in 60 mL acetone, treated with 2,2-dimethoxypropane (60 mL) and MsOH (1.23 mL, 19.09 mmol). The mixture was stirred at rt for overnight. Triethylamine was added to quench the reaction and the mixture was concentrated under reduced pressure. The residue was partitioned between CHCl3 and water; the organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 10% MeOH in EtOAc to give compound 48.3 (2.12 g, 100% yield).

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was partitioned between CHCl3 and water
  5. customthe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. washeluting with 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-71a393cd418848049cddaae966f630cc
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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