Triphenylphosphine → HCID 86601695, compound

HRID 1785945Notes

Reaction equation

HRID 1785945 reaction equation
I[C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C@H:11]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:10][C@@H:9]2[CH3:29])=[O:7])=[CH:4][CH:3]=1.[CH2:32]([O:34][C:35](=[O:40])[CH2:36][CH2:37][CH:38]=[CH2:39])[CH3:33].C([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:21]([O:20][C:19]([NH:18][C@H:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]([C:6]([C:5]2[CH:30]=[CH:31][C:2](/[CH:39]=[CH:38]/[CH2:37][CH2:36][C:35]([O:34][CH2:32][CH3:33])=[O:40])=[CH:3][CH:4]=2)=[O:7])[C@@H:9]([CH3:29])[CH2:10]1)=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 74786Ethyl 4-pentenoateHCID 517044Potassium AcetateHCID 86601696HCID 86601696, compound

Product 1

HCID 86601695HCID 86601695, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl [(2S,4R)-1-(4-iodobenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]carbamate (0.6 g, 1.14 mmol) in DMF (15 mL) at room temperature was added pent-4-enoic acid ethyl ester (0.292 g, 2.28 mmol), potassium acetate (0.67 g, 6.84 mmol), palladium acetate (0.05 g, 0.228 mmol), tetrabutylammonium chloride (0.32 g, 1.14 mmol), and triphenylphosphine (0.06 g, 0.228 mmol). The mixture was stirred at room temperature for 1 hour and then heated to 70° C. for 3 hours. The mixture was concentrated and ethyl acetate was added. The solution was washed with water, dried and concentrated. The residue was purified by silica gel chromatography (70% CH2Cl2/30% EtOAc) to afford ethyl (4E)-5-(4-{[(2S,4R)-4-{[(benzyloxy)carbonyl]amino}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)pent-4-enoate (0.5 g, 83%), which was further converted into ethyl 5-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)pentanoate following general procedure G.

Workup

  1. temperatureheated to 70° C. for 3 hours
  2. concentrationThe mixture was concentrated
  3. additionethyl acetate was added
  4. washThe solution was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (70% CH2Cl2/30% EtOAc)

Sources & evidence

ORD record
ord-427b9a5f1e954eb8a5c3958395bcb62c
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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