Boron trifluoride etherate → HCID 13422884, compound

HRID 2290419Notes

Reaction equation

HRID 2290419 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](=[O:35])[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C([O-])(O)=O.[Na+]>O1CCCC1>[C:16]([NH:17][C@@H:18]1[C@@H:21]([O:24][CH2:25][C:26](=[O:35])[CH2:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[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 516892Sodium BicarbonateHCID 13276951HCID 13276951, compoundHCID 13422882HCID 13422882, compound

Product 1

HCID 13422884HCID 13422884, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 ul of boron trifluoride etherate were added to a suspension of 216 mg (1.15 mmols) of (1R, 5S)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one and 400 mg (2.3 mmols) of freshly prepared tert.-butyl 4-hydroxyacetoacetate in 4 ml of anhydrous tetrahydrofuran at room temperature. After a short time a clear, light yellow solution formed, which was stirred for 0.5 hour at room temperature. It was then poured into dilute NaHCO3 solution. The mixture was extracted with methylene chloride, washed with water and dried over magnesium sulphate. After the solvent had been evaporated off in vacuo and the residue had been chromatographed on 60 g of silica gel (toluene:ethyl acetate 1:3), 128 mg (31%) of tert.-butyl 4-[3(R)-benzoylamino-2-azetidinon-4(R)-yloxy]acetoacetate were obtained as colorless crystals, melting point: 142° C., RF : 0.36 (toluene:ethyl acetate 1:4), [α]D20 =32.24° (0.955 percent in CHCl3).

Workup

  1. customAfter a short time a clear, light yellow solution formed
  2. extractionThe mixture was extracted with methylene chloride
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customAfter the solvent had been evaporated off in vacuo
  6. customthe residue had been chromatographed on 60 g of silica gel (toluene:ethyl acetate 1:3)

Sources & evidence

ORD record
ord-d92833bab29f4ff4bc3b11da681e20b2
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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