Hydrochloric Acid → HCID 22002639, compound

HRID 325182Notes

Reaction equation

HRID 325182 reaction equation
[OH:1][C:2]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.N1C=CC=CC=1.[C:23]1([CH2:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1CCN2C(=NCCC2)CC1.Cl>C(Cl)Cl>[CH3:16][S:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[C:2]3([CH2:6][CH2:5][CH2:4][CH2:3]3)[O:1][C:30](=[O:31])[C:29]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22002658HCID 22002658, compound

Product 1

HCID 22002639HCID 22002639, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the alcohol from Step 2 (924 mg, 3.91 mmol) in 10 mL CH2Cl2 at 0° C. was added pyridine (928 mg, 11.7 mmol) followed by phenylacetyl chloride (1.51 g, 9.77 mmol). The ice bath was removed and the mixture was stirred at room temperature for 15 h. Aq. NH4Cl (100 mL) was added and the mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was dissolved in 16 mL CH2Cl2, DBU (595 mg, 3.91 mmol) was added and the brown solution was stirred at room temperature for 0.5 h. 5% aq. HCl (100 mL) was added and the mixture was extracted with EtOAc (4×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give 1.40 g (quantitative) of the title compound as a yellow solid, used directly in the next step. An analytical sample had mp. 147-148° C. after stirring with Et2O/hexane (2:1).

Workup

  1. customThe ice bath was removed
  2. additionAq. NH4Cl (100 mL) was added
  3. extractionthe mixture was extracted with EtOAc (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in 16 mL CH2Cl2
  9. stirringthe brown solution was stirred at room temperature for 0.5 h
  10. extractionthe mixture was extracted with EtOAc (4×50 mL)
  11. washThe combined organic layers were washed with brine
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-83f71260f0ba4bf18814f868bc604c48
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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