Triethylamine → HCID 66934470, compound

HRID 1366322Notes

Reaction equation

HRID 1366322 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25](=[O:57])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C@@H:34]2[C@@H:37]([S:38]SC3C([N+]([O-])=O)=CC=CN=3)[C:36](=[O:49])[N:35]2[C:50]2[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=2)=[CH:30][CH:29]=1)([CH3:23])([CH3:22])[CH3:21].CCN(CC)CC.Br[CH2:66][C:67]([C:69]1[CH:77]=[CH:76][C:72]2[CH2:73][CH2:74][O:75][C:71]=2[CH:70]=1)=[O:68]>CC(C)=O.O>[C:20]([O:24][C:25](=[O:57])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C@@H:34]2[C@@H:37]([S:38][CH2:66][C:67]([C:69]3[CH:77]=[CH:76][C:72]4[CH2:73][CH2:74][O:75][C:71]=4[CH:70]=3)=[O:68])[C:36](=[O:49])[N:35]2[C:50]2[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=2)=[CH:30][CH:29]=1)([CH3:21])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86639220{4-[(2R,3R)-1-(4-fluoro-phenyl)-3-(3-nitro-pyridin-2-yldisulfanyl)-4-oxo-azetidin-2-yl]-phenoxy}-acetic acid tert-butyl esterHCID 866420612-Bromo-1-(2,3-dihydrobenzofuran-6-YL)ethan-1-one

Product 1

HCID 66934470HCID 66934470, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Triphenyl phosphine (50 mg, 0.191 mmol) was added to a solution of {4-[(2R,3R)-1-(4-fluoro-phenyl)-3-(3-nitro-pyridin-2-yldisulfanyl)-4-oxo-azetidin-2-yl]-phenoxy}-acetic acid tert-butyl ester (100 mg, 0.179 mmol) in acetone/water (3 mL/0.5 mL) at room temperature. The mixture was stirred for 15 min. The solvent was removed under reduced pressure and the residue was dissolved in DCM (3 mL). Et3N (75 μL, 0.534 mmol) and 2-bromo-1-(2,3-dihydro-benzofuran-6-yl)-ethanone (91 mg, 0.377 mmol) were added and the solution was stirred at room temperature for 16 h. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC using a gradient of 40-80% MeCN in a 0.1M ammonium acetate buffer as eluent. The pure fractions were pooled and most of the MeCN was removed under reduced pressure. The residue was extracted with EtOAc and the organic layer was washed with brine, dried over MgSO4 and concentrated. The title compound was obtained.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DCM (3 mL)
  3. stirringthe solution was stirred at room temperature for 16 h
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by preparative HPLC
  6. customwas removed under reduced pressure
  7. extractionThe residue was extracted with EtOAc
  8. washthe organic layer was washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4d7875dc4ffd4fd0b0dfb1c85cfb7295
Source dataset
uspto-grants-2011_02
Patent number
US07893048B2

Reaction notes

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