Hydrochloric Acid → HCID 18189442, compound

HRID 1358131Notes

Reaction equation

HRID 1358131 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:11]3[CH:13]=[CH:14][C:15]([CH2:17][S:18]([NH2:21])(=[O:20])=[O:19])=[CH:16][C:10]=3[CH:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([O:30]CC)=[O:29])[CH:23]=3)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[Li+].[OH-].Cl.C(OCC)(=O)C>C1COCC1.C(O)C>[CH3:1][O:2][C:3]1[C:12]2[C:11]3[CH:13]=[CH:14][C:15]([CH2:17][S:18]([NH2:21])(=[O:20])=[O:19])=[CH:16][C:10]=3[CH:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([OH:30])=[O:29])[CH:23]=3)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 18188707HCID 18188707, compound

Product 1

HCID 18189442HCID 18189442, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 51 (0.34 g, 0.76 mmol) in THF (5 mL) and ethanol (5 mL) was treated with a solution of 10% LiOH (5 mL), stirred at room temperature for 20 hours, and poured into a mixture of ice, 1M HCl (50 mL) and ethyl acetate (50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate. The extract was dried (Na2SO4), filtered, and concentrated to provide the desired product.(0.26 g, 80%) as a white solid MS (ESI(−)Q1MS) m/z 424 (M−H)−.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe extract was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1af0c384220e4a6987deba96304a2e8a
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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