Triphenylphosphine → benzyl (2S)-2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}-3-phenylpropanoate

HRID 1094177Notes

Reaction equation

HRID 1094177 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][C@H:16]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:53]1([NH:59][C:60]2[CH:69]=[C:68]3[C:63]([C:64](=[O:77])[C:65](CO)=[CH:66][N:67]3[CH:70]3[CH2:74][CH2:73][CH2:72][CH2:71]3)=[CH:62][C:61]=2[F:78])[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1>O.ClCCl>[CH:53]1([NH:59][C:60]2[CH:69]=[C:68]3[C:63]([C:64](=[O:77])[C:65]([O:15][C@@H:16]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])=[CH:66][N:67]3[CH:70]3[CH2:71][CH2:72][CH2:73][CH2:74]3)=[CH:62][C:61]=2[F:78])[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 9992574Benzyl (R)-(+)-2-hydroxy-3-phenylpropionateHCID 66636954HCID 66636954, compound

Product 1

HCID 66636900benzyl (2S)-2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}-3-phenylpropanoateYield 55.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

213 μl of diisopropyl azodicarboxylate was added to a 5.0 ml dichloromethane solution of 263 mg of benzyl (2R)-2-hydroxy-3-phenylpropanoate and 270 mg of triphenylphosphine at 0° C., followed by stirring for 15 minutes. Then, 177 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-(hydroxymethyl)quinolin-4(1H)-one was added thereto, followed by stirring at room temperature for 4 hours. Water was added to the reaction mixture, followed by extraction with EtOAc and washing with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate and subsequent evaporation under a reduced pressure, the residue was purified by silica gel column chromatography to obtain 160 mg of benzyl (2S)-2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}-3-phenylpropanoate.

Workup

  1. stirringby stirring at room temperature for 4 hours
  2. extractionfollowed by extraction with EtOAc
  3. washwashing with aqueous saturated sodium chloride
  4. dry with materialAfter drying over anhydrous sodium sulfate and subsequent evaporation under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ea0531b48e8499b85f2be8cb8ca5619
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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