Triphenylphosphine → N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-6-{4-[3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenyl}hex-5-enamide

HRID 1612555Notes

Reaction equation

HRID 1612555 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:10](=[O:19])[CH:9]2[CH2:20][CH2:21][CH:22]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.[CH3:38][N:39]([CH2:47][CH:48]([OH:57])[CH:49]([OH:56])[CH:50]([OH:55])[CH:51]([OH:54])[CH2:52][OH:53])[C:40](=[O:46])[CH2:41][CH2:42][CH2:43][CH:44]=[CH2:45].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:38][N:39]([CH2:47][CH:48]([OH:57])[CH:49]([OH:56])[CH:50]([OH:55])[CH:51]([OH:54])[CH2:52][OH:53])[C:40](=[O:46])[CH2:41][CH2:42][CH2:43][CH:44]=[CH:45][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:9]([CH2:20][CH2:21][CH:22]([O:30][Si:31]([C:34]([CH3:35])([CH3:37])[CH3:36])([CH3:32])[CH3:33])[C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[C:10](=[O:19])[N:11]2[C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 22252040N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)hex-5-enamideHCID 222520774-(4-Bromophenyl)-3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)azetidin-2-one

Product 1

HCID 68552127N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-6-{4-[3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenyl}hex-5-enamide

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

110 mg of 4-(4-bromophenyl)-3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)azetidin-2-one and 136 mg of N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-hex-5-enamide are initially charged in 300 μl of triethylamine under argon in a closed tube which had been heated thoroughly beforehand. After addition of 6 mg of palladium acetate and 14 mg of triphenylphosphine, the mixture is stirred at 100° C. for 4 h. The reaction mixture is then taken up in dichloromethane, filtered and concentrated using a rotary evaporator. Purification of the residue using an SiO2 cartridge (dichloromethane/methanol 20:1–5:1) gives the product. C43H58F2N2O8Si (796)

Workup

  1. temperaturehad been heated thoroughly
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customa rotary evaporator
  5. customPurification of the residue
  6. customgives the product

Sources & evidence

ORD record
ord-b4c83dad29934657998d58d7fb3ca921
Source dataset
uspto-grants-2006_01
Patent number
US06992067B2

Reaction notes

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