Triphenylphosphine → HCID 86708065, compound

HRID 1524362Notes

Reaction equation

HRID 1524362 reaction equation
[N:1]([CH2:4][C:5]([F:43])([F:42])[CH2:6][CH2:7][C@H:8]([N:18]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C:5]([F:43])([F:42])[CH2:6][CH2:7][C@H:8]([N:18]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[S:19]([C:22]1[CH:23]=[CH:24][C:25]([CH2:28][O:29][Si:30]([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:31])[CH3:32])=[CH:26][CH:27]=1)(=[O:21])=[O:20])[CH2:9][O:10][Si:11]([C:14]([CH3:16])([CH3:15])[CH3:17])([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86708064HCID 86708064, compound

Product 1

HCID 86708065HCID 86708065, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the material from Step 9 (60 mg, 0.09 mmol) in THF (1.7 mL) and water (86 μL) was added triphenylphosphine (50 mg, 0.19 mmol). The reaction mixture was stirred at room temperature for 2 hours. Then additional water (86 μL) was added, the reaction mixture was heated at reflux for 5 hours. Upon cooling to room temperature, the reaction mixture was concentrated to dryness in vacuo and the residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 42 mg of the title compound. LCMS (M+Na)=637.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 5 hours
  3. temperatureUpon cooling to room temperature
  4. concentrationthe reaction mixture was concentrated to dryness in vacuo
  5. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d38d69afdc2d4803940939e2f97bf1b3
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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