Hydrochloric Acid → HCID 66594577, compound

HRID 1093517Notes

Reaction equation

HRID 1093517 reaction equation
C(OC(=O)[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=3)=[C:20]([C:35]#[N:36])[CH:19]=2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(C)(C)C.[OH-].[Na+].[ClH:40].O1CCOCC1>O1CCCC1.O.FC(F)(F)C(O)=O.C(Cl)Cl>[ClH:40].[NH2:7][C:8]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=2)=[C:20]([C:35]#[N:36])[CH:19]=1)([CH2:13][OH:12])[CH2:9][OH:10]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 59407763HCID 59407763, compound

Product 1

HCID 66594577HCID 66594577, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 208-2 (0.360 g) was dissolved in a mixed solvent of tetrahydrofuran (4 ml) and water (1 ml), trifluoroacetic acid (1 ml) was added, and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added 1M aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a yellow oil. To a solution of the yellow oil in methylene chloride (5 ml) was added hydrogen chloride containing dioxane (4 mol/l, 5 ml), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated, and the residue was washed with diethyl ether to give a white powder. The white powder was purified by HPLC, the obtained residue was converted to hydrochloride by adding hydrogen chloride containing ether (1 mol/l, 15 ml), and the precipitate was collected by filtration and dried to give the object product (110 mg) as a pale-brown powder.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto give a yellow oil
  7. stirringthe mixture was stirred at room temperature for 3 hr
  8. concentrationThe reaction mixture was concentrated
  9. washthe residue was washed with diethyl ether
  10. customto give a white powder
  11. customThe white powder was purified by HPLC
  12. additionby adding hydrogen chloride
  13. additioncontaining ether (1 mol/l, 15 ml)
  14. filtrationthe precipitate was collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-c41b115fd77b4f439e2c053239dd81c6
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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