HCID 72324673, compound → HCID 57446121, compound

HRID 1803813Notes

Reaction equation

HRID 1803813 reaction equation
[N:1]([CH2:4][C:5]([NH:7][CH:8]([CH2:13][S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C2CCCCO2)[CH:17]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:6])=[N+:2]=[N-:3]>Cl.CO>[N:1]([CH2:4][C:5]([NH:7][CH:8]([CH2:13][S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:6])=[N+:2]=[N-:3]

Participants

4

Reactant 1

HCID 72324673HCID 72324673, compound

Product 1

HCID 57446121HCID 57446121, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

Few drops of conc. HCl (5 drops) were added to the 44 (0.25 g) in methanol and stirred for 30 min until no starting material was seen by LCMS. After evaporation of methanol, brine was added to the reaction mixture and extracted with ethyl acetate, dried over MgSO4, concentrated and chromatographed (Hexanes/EtOAc) then 5% methanol/methylene chloride) to obtain the 0.2 g of 45 as colorless oil in quantitative yield.

Workup

  1. customAfter evaporation of methanol, brine
  2. additionwas added to the reaction mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed (Hexanes/EtOAc)

Sources & evidence

ORD record
ord-bc6976e202bf450d879753526861d8d6
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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