Trifluoroacetic acid → HCID 11527791, compound

HRID 1241527Notes

Reaction equation

HRID 1241527 reaction equation
[Si]([O:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[N:13]([C:16](=[P:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C@@H:12]1[CH2:49][C:50]([C:52]1[CH:64]=[CH:63][C:55]([C:56]([O:58]C(C)(C)C)=[O:57])=[CH:54][CH:53]=1)=[O:51])[CH3:10])(C(C)(C)C)(C)C.FC(F)(F)C(O)=O>>[OH:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[N:13]([C:16](=[P:30]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:18])[C@@H:12]1[CH2:49][C:50]([C:52]1[CH:53]=[CH:54][C:55]([C:56]([OH:58])=[O:57])=[CH:63][CH:64]=1)=[O:51])[CH3:10]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11614914HCID 11614914, compound

Product 1

HCID 11527791HCID 11527791, compoundYield 99.8%

Procedure

To tert-butyl 4-({(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-ethyl)-1-[2-[(4-nitrobenzyl)oxy]-2-oxo-1-(triphenylphosphoranylidene)ethyl]-4-oxo-2-azetidinyl}acetyl)benzoate (2.703 g, 3.00 mmol) obtained in Step a) was added trifluoroacetic acid (9 ml) under ice-cooling and dissolved it, and the mixture was further stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure, and the residue was dissolved again in chloroform/toluene, and concentrated again under reduced pressure. To the residue was added hexane/diethyl ether, and the mixture was subjected to decantation (three times), and the resulting solid was collected by filtration, washed with hexane, and dried under reduced pressure to give 4-({(2R,3S)-3-[(1R)-1-hydroxyethyl]-1-[2-[(4-nitrobenzyl)oxy]-2-oxo-1-(triphenylphosphoranylidene)ethyl]-4-oxo-2-azetidinyl}acetyl)benzoic acid (2.187 g).

Workup

  1. temperaturecooling
  2. dissolutiondissolved it
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved again in chloroform/toluene
  5. concentrationconcentrated again under reduced pressure
  6. additionTo the residue was added hexane/diethyl ether
  7. filtrationthe resulting solid was collected by filtration
  8. washwashed with hexane
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-d462d6cfd17641d4b60a551922543f01
Source dataset
uspto-grants-2006_10
Patent number
US07115595B2

Reaction notes

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