Phosphonium, hexyltriphenyl-, bromide (1:1) → HCID 68818416, compound

HRID 732591

Reaction equation

HRID 732591 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].CC(C)([O-])C.[K+].[C:33]([O:37][C:38]([N:40]1[CH2:44][C:43](=O)[CH2:42][C@@H:41]1[C@H:46]1[O:50][C:49]([CH3:52])([CH3:51])[N:48]([C:53](=[O:55])[CH3:54])[C@H:47]1[CH2:56][C:57]1[CH:62]=[C:61]([F:63])[CH:60]=[C:59]([F:64])[CH:58]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>C1COCC1>[C:33]([O:37][C:38]([N:40]1[CH2:44]/[C:43](=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])/[CH2:42][C@@H:41]1[C@H:46]1[O:50][C:49]([CH3:51])([CH3:52])[N:48]([C:53](=[O:55])[CH3:54])[C@H:47]1[CH2:56][C:57]1[CH:58]=[C:59]([F:64])[CH:60]=[C:61]([F:63])[CH:62]=1)=[O:39])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 2724569Phosphonium, hexyltriphenyl-, bromide (1:1)HCID 23665647Potassium tert-butoxideHCID 68814480HCID 68814480, compound

Product 1

HCID 68818416HCID 68818416, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Place under argon a suspension of n-hexyltriphenylphosphonium bromide (0.420 g, 1 mmol) in 10 mL of dry THF. Add potassium tert-butoxide (0.112 g, 1 mmol). Stir the mixture for 1 h. Add a solution of (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (0.045 g, 0.1 mmol) in 5 mL of dry THF. Stir the mixture overnight. Add water, extract with diethyl ether, dry over MgSO4, concentrate under reduced pressure and purify (silica gel chromatography, eluting with ethyl ether:hexane mixtures) to give the title compound (0.04 g, 76%).

Workup

  1. stirringStir the mixture overnight
  2. extractionAdd water, extract with diethyl ether
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate under reduced pressure
  5. custompurify
  6. wash(silica gel chromatography, eluting with ethyl ether:hexane mixtures)

Sources & evidence

ORD record
ord-2818c567f17b4da281a5882559522ab8
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Linked notes

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