Water → HCID 68844294, compound

HRID 1723700Notes

Reaction equation

HRID 1723700 reaction equation
[N:1]([C@H:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][C@@H:5]1[N:16]1[CH2:21][C:20]([F:23])([F:22])[CH2:19][CH2:18][C:17]1=[O:24])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][C@H:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:6][C@@H:5]1[N:16]1[CH2:21][C:20]([F:23])([F:22])[CH2:19][CH2:18][C:17]1=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86617111HCID 86617111, compound

Product 1

HCID 68844294HCID 68844294, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 7 (8.50 g, 25.3 mmol) in tetrahydrofuran (85 mL) was added triphenylphosphine (6.65 g, 25.3 mmol) and H2O (0.91 g, 50.7 mmol). The solution was stirred at reflux for 3 hours and then cooled to room temperature and concentrated. The residue was dissolved in 4.0 N aqueous HCl (200 mL) and extracted with chloroform (200 mL). The aqueous layer was basified to pH 10 with concentrated aqueous ammonium hydroxide solution and the resulting mixture was extracted with chloroform (2×300 mL). The combined organic extracts were dried over sodium sulfate and concentrated to afford 7.84 g (99%) of the product as a solid. MS m/z 310.3 (AP+100).

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 4.0 N aqueous HCl (200 mL)
  4. extractionextracted with chloroform (200 mL)
  5. extractionthe resulting mixture was extracted with chloroform (2×300 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c7ffca0d4dd749d590eb4793d1cb4e94
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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