Triethyl phosphonoacetate → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]-1,4-oxazepane-4-carboxylate

HRID 1022672Notes

Reaction equation

HRID 1022672 reaction equation
[Cl-].[Li+].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[CH2:25]([O:27][C:28](=[O:38])[CH2:29]P(OCC)(OCC)=O)[CH3:26].[Cl:39][C:40]1[CH:41]=[C:42]([C@@H:47]2[O:53][CH2:52][CH2:51][N:50]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:49][C@H:48]2[CH:61]=O)[CH:43]=[CH:44][C:45]=1[Cl:46]>C(#N)C>[Cl:39][C:40]1[CH:41]=[C:42]([C@@H:47]2[O:53][CH2:52][CH2:51][N:50]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:49][C@H:48]2/[CH:61]=[CH:29]/[C:28]([O:27][CH2:25][CH3:26])=[O:38])[CH:43]=[CH:44][C:45]=1[Cl:46]

Participants

6

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 433294Lithium ChlorideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 86663853tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976531tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]-1,4-oxazepane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of lithium chloride (136 mg) and diazabicycloundecene (0.403 mL) in acetonitrile (26.7 mL) was added ethyl(diethoxyphosphoryl)acetate (0.642 mL), and the mixture was stirred at 20 min. tert-Butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate (1.00 g) was added and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, distilled water was added, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (902 mg).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. distillationdistilled water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with distilled water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1cadf7c38a29422cac3f4ee99ee9b35c
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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