Boron trifluoride etherate → HCID 13422895, compound

HRID 2290425Notes

Reaction equation

HRID 2290425 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.[OH:24][CH2:25][C:26]#[C:27][C:28]([O:30][CH3:31])=[O:29].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:16]([NH:17][C@@H:18]1[C@@H:21]([O:24][CH2:25][C:26]#[C:27][C:28]([O:30][CH3:31])=[O:29])[NH:20][C:19]1=[O:23])(=[O:22])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 325086Methyl 4-hydroxybut-2-ynoateHCID 516892Sodium BicarbonateHCID 13276951HCID 13276951, compound

Product 1

HCID 13422895HCID 13422895, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.41 ml of boron trifluoride etherate was added to a suspension of 4.70 g (25 mmols) of (1R, 5S)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one and 14.3 g (125 mmols--5 equivalents) of methyl 4-hydroxy-2-butinoate (R. A. Earl, Organic Synthese 60, 81) in 40 ml of anhydrous methylene chloride at room temperature. The mixture was stirred at room temperature for 1 hour, whereupon a clear solution formed. The solution was then poured into dilute NaHCO3 solution, the mixture was extracted with methylene chloride and the extracts were washed with water and dried over MgSO4. After the solvent had been evaporated off in vacuo and the residue had been filtered on 120 g of silica gel (toluene:ethyl acetate 2:3), 4.74 g (63%) of methyl 4-[3(R)-benzoylamino-2-azetidinon-4(R)-yloxy]-2-butinoate were obtained as colorless crystals, melting point: 142°-143° C, RF : 0.29 (toluene:ethyl acetate 2:3), [α]D20 =18.37° (1.0345 percent in acetone).

Workup

  1. customat room temperature
  2. customformed
  3. extractionthe mixture was extracted with methylene chloride
  4. washthe extracts were washed with water
  5. dry with materialdried over MgSO4
  6. customAfter the solvent had been evaporated off in vacuo
  7. filtrationthe residue had been filtered on 120 g of silica gel (toluene:ethyl acetate 2:3)

Sources & evidence

ORD record
ord-48f199996c6d4bc28d8a243631a83ff8
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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