Triphenylphosphine → HCID 66861047, compound

HRID 251861Notes

Reaction equation

HRID 251861 reaction equation
Cl.[N:2]([CH2:5][C:6]([N:8]1[CH:13]([CH3:14])[CH2:12][N:11]([C:15]2[C:24]([O:25][CH3:26])=[C:23]3[C:18]([C:19](=[O:42])[C:20]([C:30]([NH:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=4[Cl:41])=[O:31])=[CH:21][N:22]3[CH:27]3[CH2:29][CH2:28]3)=[CH:17][C:16]=2[F:43])[CH2:10][CH:9]1[CH3:44])=[O:7])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[ClH:40].[CH:27]1([N:22]2[C:23]3[C:18](=[CH:17][C:16]([F:43])=[C:15]([N:11]4[CH2:10][CH:9]([CH3:44])[N:8]([C:6](=[O:7])[CH2:5][NH2:2])[CH:13]([CH3:14])[CH2:12]4)[C:24]=3[O:25][CH3:26])[C:19](=[O:42])[C:20]([C:30]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=3[Cl:41])=[O:31])=[CH:21]2)[CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 131728611HCID 131728611, compound

Product 1

HCID 66861047HCID 66861047, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

46.0 mg (0.07 mmol) of the compound of Example 82A are provided in 2 ml of tetrahydrofuran, the solution is cooled to 0° C., 21.1 mg (0.08 mmol) of triphenylphosphine, dissolved in 1 ml of tetrahydrofuran are added dropwise, the reaction mixture is warmed to room temperature and stirred over night at this temperature. For the work-up the solvent is removed completely on a rotary evaporator, the residue is prepurified by preparative RP-HPLC (Method 6) and after fine purification by column chromatography on silica gel 60 (eluent: dichloromethane:ethanol 90:10) and concentrating the fractions with the addition of hydrochloric acid 24 mg of the target compound are obtained.

Workup

  1. additionare added dropwise
  2. temperaturethe reaction mixture is warmed to room temperature
  3. customFor the work-up the solvent is removed completely on a rotary evaporator
  4. customafter fine purification by column chromatography on silica gel 60 (eluent: dichloromethane:ethanol 90:10)
  5. concentrationconcentrating the fractions
  6. additionwith the addition of hydrochloric acid 24 mg of the target compound
  7. customare obtained

Sources & evidence

ORD record
ord-7a3d68777aa74b899be93167fe39fc84
Source dataset
uspto-grants-2011_01
Patent number
US07867992B2

Reaction notes

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