Boron trifluoride etherate → HCID 11760406, compound

HRID 2288904Notes

Reaction equation

HRID 2288904 reaction equation
[C:1]([NH:11][C@H:12]([C:21]([OH:23])=[O:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1CCCCC1.ClC(Cl)(Cl)C(=N)O[C:34]([CH3:37])([CH3:36])[CH3:35].B(F)(F)F.CCOCC>ClCCl>[C:1]([NH:11][C@H:12]([C:21]([O:23][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherate2×HCID 8078CyclohexaneHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate2×HCID 7010616Z-Homophe-OH

Product 1

HCID 11760406HCID 11760406, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, to a solution of (N-carbobenzyloxy)-(L)-homophenylalanine (0.476 g, 1.52 mmol) in anhydrous dichloromethane (3.5 mL) was added anhydrous cyclohexane (7 mL). To this clear solution was added with vigourous stirring tert-butyl 2,2,2-trichloroacetimidate (0.30 mL, 1.67 mmol) followed by dropwise addition of boron trifluoride diethyl etherate (30 mL). After stirring at room temperature for 2 hr, additional tert-butyl 2,2,2-trichloroacetimidate (0.45 mL, 2.50 mmol) and boron trifluoride diethyl etherate (45 mL) were added to the reaction mixture and stirring was continued overnight at room temperature. The reaction mixture was filtered through a pad of celite, and the residue was washed with ether. The solvent was removed from the filtrate by rotoevaporation and the crude product was purified by flash column chromatography on silica gel eluted with 2-6% ethyl acetate in hexane to afford the title compound (211 mg, 38% yield), homogeneous by TLC (4/1 hexane/ethyl acetate).

Workup

  1. additionTo this clear solution was added
  2. stirringstirring
  3. waitwas continued overnight at room temperature
  4. filtrationThe reaction mixture was filtered through a pad of celite
  5. washthe residue was washed with ether
  6. customThe solvent was removed from the filtrate by rotoevaporation
  7. customthe crude product was purified by flash column chromatography on silica gel
  8. washeluted with 2-6% ethyl acetate in hexane

Sources & evidence

ORD record
ord-daa8e3b09c774657b9d650167911984e
Source dataset
uspto-grants-2000_07
Patent number
US06090841

Reaction notes

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