Triphenylphosphine → HCID 118022418, compound

HRID 575789Notes

Reaction equation

HRID 575789 reaction equation
[C:1]1([C@@H:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:30]1[CH:31]=[C:32]([C:40]2[CH:41]=[C:42]([CH3:48])[C:43](=[O:47])[N:44]([CH3:46])[CH:45]=2)[CH:33]=[C:34]([S:36]([CH3:39])(=[O:38])=[O:37])[CH:35]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:46][N:44]1[CH:45]=[C:40]([C:32]2[CH:31]=[C:30]([O:9][C@@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH3:8])[CH:35]=[C:34]([S:36]([CH3:39])(=[O:38])=[O:37])[CH:33]=2)[CH:41]=[C:42]([CH3:48])[C:43]1=[O:47]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 4431351-Phenylethanol, (S)-HCID 5363146Diisopropyl azodicarboxylateHCID 118021370HCID 118021370, compound

Product 1

HCID 118022418HCID 118022418, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1S)-1-phenylethan-1-ol (14 mg, 0.11 mmol) in THF (1 mL) stirred at rt under an atmosphere of nitrogen was treated with triphenylphosphine (38 mg, 0.15 mmol) and 5-(3-hydroxy-5-methylsulfonylphenyl)-1,3-dimethylpyridin-2-one (33 mg, 0.11 mmol). After 30 min, the reaction mixture was treated with DIAD (29 mg, 0.15 mmol). The nitrogen inlet was removed and the mixture was stirred (closed system) for 18 h. After the reaction mixture was diluted with EtOAc (10 ml), it was washed with water, saturated sodium bicarbonate solution (aq), dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was diluted with ACN (1 mL) and was purified by prep-HPLC to afford the title compound (21 mg, 48%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.61 (d. J=6.4, 3 H) 2.08 (s, 3H) 3.20 (s, 3H) 3.52 (s, 3H) 5.70-5.80 (q. J=6.4, 1H) 7.23-7.31 (m, 2H) 7.35-7.41 (m, 2H) 7.44-7.51 (m, 3H) 7.56-7.63 (m, 1H) 7.73-7.80 (m, 1H) 8.08-8.15 (m, 1H). LCMS (M+H)+=398.

Workup

  1. customThe nitrogen inlet was removed
  2. custom(closed system) for 18 h
  3. additionAfter the reaction mixture was diluted with EtOAc (10 ml), it
  4. washwas washed with water, saturated sodium bicarbonate solution (aq)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionThe crude residue was diluted with ACN (1 mL)
  9. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-eaea5fdbedf84a02adbce9f9d2569109
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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