HCID 69271340, compound → HCID 69271247, compound

HRID 2222382Notes

Reaction equation

HRID 2222382 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]3[O:29][C@H:28]([CH2:30][OH:31])[C@@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]3[OH:23])=[CH:17][CH:16]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[P:32](Cl)(=[O:40])([O-:39])[O:33]CC(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[CH:16]=[CH:17][C:18]([C@@H:21]3[O:29][C@H:28]([CH2:30][O:31][P:32]([OH:40])([OH:39])=[O:33])[C@@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]3[OH:23])=[CH:19][CH:20]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 69271340HCID 69271340, compoundHCID 85564173HCID 85564173, compound

Product 1

HCID 69271247HCID 69271247, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 44 (100 mg) and (2,2,2-trichloroethyl) phosphorochloridate (256 mg) were dissolved in pyridine (2 mL), and the resultant solution was stirred for two hours. After completion of reaction, the resultant reaction mixture was concentrated to dryness under reduced pressure, followed by purification by means of silica gel chromatography employing a chloroform/methanol system. The thus-purified product was dissolved in a pyridine-acetic acid (4:1) solvent mixture, and zinc powder (140 mg) was added to the resultant solution, followed by stirring for two hours. After completion of reaction, the resultant reaction mixture was concentrated to dryness under reduced pressure, followed by purification by means of silica gel chromatography employing a chloroform/methanol system, to thereby produce the target product (83 mg, yield: 70%).

Workup

  1. customAfter completion of reaction
  2. customthe resultant reaction mixture
  3. concentrationwas concentrated to dryness under reduced pressure
  4. customfollowed by purification by means of silica gel chromatography
  5. dissolutionThe thus-purified product was dissolved in a pyridine-acetic acid (4:1) solvent mixture, and zinc powder (140 mg)
  6. additionwas added to the resultant solution
  7. customAfter completion of reaction
  8. customthe resultant reaction mixture
  9. concentrationwas concentrated to dryness under reduced pressure
  10. customfollowed by purification by means of silica gel chromatography

Sources & evidence

ORD record
ord-a01ce0428b0549558f3ce32d8460230a
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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