HCID 68844761, compound → HCID 72458935, compound

HRID 227568Notes

Reaction equation

HRID 227568 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH:13]=[C:14]([P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[F:15])[CH2:11][O:10]C1(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)NC(C)(C1NC(C2C=CC(CCCCCCCC)=CC=2)=CN=1)COP(OC(C)(C)C)(OC(C)(C)C)=O)(C)(C)C>CCO>[CH2:19]([O:18][P:16]([C:14]([F:15])=[CH:13][CH:12]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:11][OH:10])(=[O:17])[O:21][CH2:22][CH3:23])[CH3:20]

Participants

4

Reactant 2

HCID 68844761HCID 68844761, compoundHCID 72458934HCID 72458934, compound

Product 1

HCID 72458935HCID 72458935, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To compound (38) (47 mg, 0.123 mmol) stirring in EtOH (1 mL) was added Dowex 50×8 (150 mg), which washed with EtOH and dried. The reaction was allowed to stir under nitrogen and at room temperature for 24 hours. The reaction mixture was filtered and the precipitate washed with excess EtOH, then concentrated in vacuo. The crude material was purified by column chromatography on SiO2 (1:1 EtOAc/Hexanes) to yield 34 mg of the expected product.

Workup

  1. washwashed with EtOH
  2. customdried
  3. filtrationThe reaction mixture was filtered
  4. washthe precipitate washed with excess EtOH
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography on SiO2 (1:1 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-64cccebb014244ca9459adfe00c4fa25
Source dataset
uspto-grants-2009_07
Patent number
US07560477B2

Reaction notes

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