Hydrochloric Acid → HCID 70298368, compound

HRID 1106906Notes

Reaction equation

HRID 1106906 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([N:23]([C:25](=[O:36])[CH2:26][C:27]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[O:29][CH:28]=2)[CH3:24])[CH2:16][N:17]2[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]2)[CH:10]=1)(C)(C)C.Cl.C(OCC)(=O)C>ClCCl.O>[O:29]1[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:27]([CH2:26][C:25]([N:23]([CH3:24])[CH:15]([C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][CH2:7][C:6]([OH:37])=[O:5])[CH2:16][N:17]2[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]2)=[O:36])=[CH:28]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 70298693HCID 70298693, compound

Product 1

HCID 70298368HCID 70298368, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 27 (0.79 g, 1.55 mmol) in dichloromethane (12 mL) and water (0.5 mL) was added HCl (2.5 mL of 4 M solution in dioxan). After stirring for 24 hours, all volatiles were removed in vacuo to give a pale pink solid. The solid was stirred with ethyl acetate (75 mL) for 2 hours, then the solvent removed by pipette. This was repeated. The resulting solid was dissolved in acetonitrile (50 mL) and all solids removed by filtration. Ethyl acetate was added until the solution became cloudy, and the precipitate was allowed to settle. All supernatant was then removed and the resulting solid dried. Yield 0.25 g.

Workup

  1. customall volatiles were removed in vacuo
  2. customto give a pale pink solid
  3. customthe solvent removed by pipette
  4. dissolutionThe resulting solid was dissolved in acetonitrile (50 mL)
  5. customall solids removed by filtration
  6. additionEthyl acetate was added until the solution
  7. customAll supernatant was then removed
  8. customthe resulting solid dried

Sources & evidence

ORD record
ord-e2e4d305402b48c493be44e658c0a962
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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