Hydrochloric Acid → HCID 86609028, compound

HRID 2104466Notes

Reaction equation

HRID 2104466 reaction equation
Cl.C([O:6][C:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[S:27])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][N:21]=2)=[O:18])[C@H:11]([NH:28][C:29]([C:31]2[S:32][C:33]3[CH2:34][N:35]([CH3:40])[CH2:36][CH2:37][C:38]=3[N:39]=2)=[O:30])[CH2:10]1)=[O:8])(C)(C)C>O1CCOCC1>[ClH:26].[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:17](=[O:18])[C:16]([NH:15][C@H:12]2[CH2:13][CH2:14][C@H:9]([C:7]([OH:8])=[O:6])[CH2:10][C@H:11]2[NH:28][C:29]([C:31]2[S:32][C:33]3[CH2:34][N:35]([CH3:40])[CH2:36][CH2:37][C:38]=3[N:39]=2)=[O:30])=[S:27])=[N:21][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57804530HCID 57804530, compound

Product 1

HCID 86609028HCID 86609028, compoundYield 170.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4N HCl in dioxane (10 mL) was added to a solution of the compound obtained in Example 377 (293 mg) in dioxane (8.0 mL), and the mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced mixture, and the residue was suspended in diisopropyl ether and then collected through filtration. The collected powder was dissolved in water and then neutralized with saturated aqueous sodium bicarbonate. The aqueous solution was extracted with methylene chloride, and the formed organic layer was washed with saturated brine and dried over sodium sulfate anhydrate, followed by concentration under reduced pressure. 1N HCl in ethanol (0.50 mL) was added to the residue, and the mixture was subjected to concentration under reduced pressure. The residue was dissolved in water, followed by freeze-drying, to thereby yield the title compound (242 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced mixture
  2. filtrationcollected through filtration
  3. dissolutionThe collected powder was dissolved in water
  4. extractionThe aqueous solution was extracted with methylene chloride
  5. washthe formed organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate anhydrate
  7. concentrationfollowed by concentration under reduced pressure
  8. addition1N HCl in ethanol (0.50 mL) was added to the residue
  9. concentrationthe mixture was subjected to concentration under reduced pressure
  10. dissolutionThe residue was dissolved in water
  11. customby freeze-drying

Sources & evidence

ORD record
ord-c123174ab84447fc90b3b981ab218323
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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