HCID 70059335, compound → HCID 70059316, compound

HRID 2230282Notes

Reaction equation

HRID 2230282 reaction equation
[C:1]([O:5][C:6](=[O:41])[C@@H:7]([NH:23]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>N1CCCCC1.ClCCl>[C:1]([O:5][C:6](=[O:41])[C@@H:7]([NH2:23])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 70059335HCID 70059335, compound

Product 1

HCID 70059316HCID 70059316, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8082PiperidineSolvent

Procedure

The product from Example H (3.90 g, 8.42 mmol) was suspended in 50 mL of 20% piperidine in dichloromethane at room temperature with stirring (2 h). The solution was concentrated under reduced pressure and partitioned between ethyl acetate and water (100 mL each) and separated. The organic layer was washed with 5% sodium bicarbonate (2×50 mL), brine (2×50 mL), dried with magnesium sulfate, filtered and concentrated under reduced pressure to an oil. The oil was purified by silica gel chromatography with ethyl acetate and methanol (3:1). Appropriate fractions were combined and concentrated under reduced pressure to a solid (1.34 g).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. custompartitioned between ethyl acetate and water (100 mL each)
  3. customseparated
  4. washThe organic layer was washed with 5% sodium bicarbonate (2×50 mL), brine (2×50 mL)
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to an oil
  8. customThe oil was purified by silica gel chromatography with ethyl acetate and methanol (3:1)
  9. concentrationconcentrated under reduced pressure to a solid (1.34 g)

Sources & evidence

ORD record
ord-0f3be5abad524da192a7bf844918b70a
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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