Boron trifluoride etherate → HCID 9798247, compound

HRID 990105Notes

Reaction equation

HRID 990105 reaction equation
C[Si](C)(C)CC[O:5][NH:6][C:7]([C@H:9]1[CH2:13][N:12]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[C:11](=[O:29])[NH:10]1)=[O:8].B(F)(F)F.CCOCC>C(Cl)Cl>[OH:5][NH:6][C:7]([C@H:9]1[CH2:13][N:12]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:19][CH:20]=2)[C:11](=[O:29])[NH:10]1)=[O:8]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 12971982HCID 12971982, compound

Product 1

HCID 9798247HCID 9798247, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4R)-1-[4-(4-fluorophenoxy)benzyl]-2-oxo-imidazolidine-4-carboxylic acid (2-trimethylsilanylethoxy)amide (85 mg, 0. 19 mmol) in methylene chloride (5 mL) was added boron trifluoride etherate (0.073 mL, 0.58 mmol). The reaction mixture was stirred at room temperature for 1.5 hours and then quenched by addition of aqueous saturated NH4Cl solution. The mixture was diluted with water and ethyl acetate and the organic phase was washed with brine, dried over MgSO4 and concentrated to a white solid. The title compound (31 mg, 47%) was isolated by recrystallization from a mixture of ethyl acetate and methanol.

Workup

  1. customquenched by addition of aqueous saturated NH4Cl solution
  2. additionThe mixture was diluted with water and ethyl acetate
  3. washthe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-5e240cbda8c04da788207cebf28c4ad5
Source dataset
uspto-grants-2002_10
Patent number
US06458822B2

Reaction notes

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