Boron trifluoride etherate → HCID 69755503, compound

HRID 1070433Notes

Reaction equation

HRID 1070433 reaction equation
C([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)(OC(C)(C)C)=O.[Cl:21]C(Cl)(Cl)C(=N)O[C:25]([CH3:28])([CH3:27])[CH3:26].B(F)(F)F.CCOCC>C(Cl)Cl.C1CCCCC1>[ClH:21].[I:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][C@@H:9]([C:18]([O:20][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:19])[NH2:8])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 2734700Tert-butyl 2,2,2-trichloroethanimidate2×HCID 2755956(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

Product 1

HCID 69755503HCID 69755503, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

To a suspension of N-Boc-4-iodo-(L)-phenylalanine (1.0 g, 2.56 mmol) in methylene chloride (7 mL) and cyclohexane (14 mL) were added t-butyl trichloroacetimidate (0.48 mL, 2.68 mmol) and boron trifluoride-etherate (48 μL). The reaction mixture was stirred for 5 hours at room temperature under a nitrogen atmosphere and then treated a second time with the same amounts of t-butyl trichloroacetimidate and boron trifluoride-etherate as above. After stirring overnight, a third addition was made, and the mixture was stirred a further 3 hours. The mixture was then filtered and the filtrate evaporated. The product was obtained pure by silica gel chromatography eluting with 10% diethyl ether in hexane; yield 650 mg. The product was treated with 1M HCl in ethyl acetate (7.3 mL) for 18 hours at room temperature. The mixture was evaporated and coevaporated several times with diethyl ether to afford the title compound; yield 522 mg.

Workup

  1. stirringAfter stirring overnight
  2. additiona third addition
  3. stirringthe mixture was stirred a further 3 hours
  4. filtrationThe mixture was then filtered
  5. customthe filtrate evaporated
  6. customThe product was obtained pure by silica gel chromatography
  7. washeluting with 10% diethyl ether in hexane
  8. additionThe product was treated with 1M HCl in ethyl acetate (7.3 mL) for 18 hours at room temperature
  9. customThe mixture was evaporated

Sources & evidence

ORD record
ord-c9eb89b446c841c68e85c6af927bb5bd
Source dataset
uspto-grants-2005_06
Patent number
US06903075B1

Reaction notes

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