Boron trifluoride etherate → HCID 56613986, compound

HRID 2290429Notes

Reaction equation

HRID 2290429 reaction equation
B(F)(F)F.CCOCC.[C:10]1([C:16]2[O:22][C@H:21]3[C@H:18]([C:19](=[O:23])[NH:20]3)[N:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N+:24](=[C:26]([C:34](=[O:37])[CH2:35][OH:36])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[N-:25].C([O-])(O)=O.[Na+]>O1CCCC1.C(Cl)Cl>[C:16]([NH:17][C@@H:18]1[C@@H:21]([O:36][CH2:35][C:34](=[O:37])[C:26](=[N+:24]=[N-:25])[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[NH:20][C:19]1=[O:23])(=[O:22])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 13276951HCID 13276951, compoundHCID 56633087HCID 56633087, compound

Product 1

HCID 56613986HCID 56613986, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

90 μl of boron trifluoride etherate were added to a suspension of 564 mg (3.0 mmol) (1R,5S)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one and 1.08 g (5.4 mmol-1.8 equiv.) tert.-butyl 2-diazo-4-hydroxy-3-oxo-butanoate in 12 ml of anhydrous tetrahydrofuran at 0° C. The cooling bath was removed and after 10 minutes a clear, light yellow solution formed. After 20 minutes it was poured into a mixture of NaHCO3 solution, ice and methylene chloride. The mixture was extracted with methylene chloride (3×), washed with water and dried over magnesium sulphate. After the solvent had been evaporated off in vacuo and the residue had been crystalized from methylene chloride-ether-pentane, 861 mg (74%) of the title compound were obtained as light yellow crystals, melting point: 98° C., RF : 0.29 (toluene:ethyl acetate 2:3). Spectroscopical data identical to Example 4.

Workup

  1. customThe cooling bath was removed and after 10 minutes a clear, light yellow solution
  2. customformed
  3. extractionThe mixture was extracted with methylene chloride (3×)
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customAfter the solvent had been evaporated off in vacuo
  7. customthe residue had been crystalized from methylene chloride-ether-pentane

Sources & evidence

ORD record
ord-1de1dc4a13af4ac5a4fedf0c7c275db0
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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