Boron trifluoride etherate → HCID 15534394, compound

HRID 1622964Notes

Reaction equation

HRID 1622964 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.ClC(Cl)(Cl)C(=N)O[C:31]([CH3:34])([CH3:33])[CH3:32].C([O-])(O)=O.[Na+]>C(Cl)Cl.C1CCCCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:17])([C:14]([O:16][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate

Product 1

HCID 15534394HCID 15534394, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent2×

Procedure

To a solution of N-[(benzyloxy)carbonyl]-2-methylalanine (1 g, 4.21 mmol) in DCM (10 ml anhydrous), cyclohexane (10 ml) at 0° C. under nitrogen was added boron trifluoride diethyl etherate (7.7 μl, catalytic). tert-Butyl 2,2,2-trichloroacetimidate (1.51 ml, 8.43 mmol) in cyclohexane (10 ml) was then added slowly over 30 minutes before allowing to warm to RT. Reaction was allowed to stir at RT for 16 hours. To the crude reaction mixture was added 190 mg of NaHCO3 and the reaction filtered. The mother liquors were concentrated in vacuo. The crude extract was purified by column chromatography (10% EtOAc in heptane) to yield the desired product (0.863 g, 70% yield).

Workup

  1. customReaction
  2. customTo the crude reaction mixture
  3. filtrationthe reaction filtered
  4. concentrationThe mother liquors were concentrated in vacuo
  5. extractionThe crude extract
  6. customwas purified by column chromatography (10% EtOAc in heptane)

Sources & evidence

ORD record
ord-a45f128fa6d14856924abfead762c2f0
Source dataset
uspto-grants-2014_07
Patent number
US08778953B2

Reaction notes

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