Hydrochloric Acid → HCID 69315473, compound

HRID 271534Notes

Reaction equation

HRID 271534 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=O)[CH2:18][CH:19]([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[CH2:33][CH2:32][C:31]3=NOC)[C:20](=[O:27])[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[O:42]1CCOCC1>CC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[O:27][C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:19]([C:28]3[CH:29]=[C:33]4[C:34](=[CH:35][CH:36]=3)[C:30](=[O:42])[CH2:31][CH2:32]4)[CH:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86760769HCID 86760769, compound

Product 1

HCID 69315473HCID 69315473, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of the product of Step 4 (4.0 g, 7.42 mmol) in 1,4-dioxane (100 ml) and acetone (250 ml) was treated with 5M hydrochloric acid (50 ml) and the mixture heated at 90° C. for 5 hours. After cooling to room temperature, the reaction was concentrated and re-dissolved in chloroform and saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried, concentrated in vacuo and purified by silica gel chromatography eluting with ethyl acetate/dichloromethane (4:6) to yield the title compound (2.50 g, 69%); MS(ES+) m/e 493 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction was concentrated
  3. dissolutionre-dissolved in chloroform
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography
  7. washeluting with ethyl acetate/dichloromethane (4:6)

Sources & evidence

ORD record
ord-62a0d8c1d24d45e4b6e1c2e85cfe99ed
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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