Boron trifluoride etherate → HCID 9883809, compound

HRID 1953052Notes

Reaction equation

HRID 1953052 reaction equation
C[Si](C)(C)CC[O:5][NH:6][C:7]([C@H:9]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)[C:11](=[O:28])[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][C@@H:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)[C:11](=[O:28])[NH:10]1)=[O:8]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 10717338HCID 10717338, compound

Product 1

HCID 9883809HCID 9883809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (2R, 4S)-4-(4-benzyloxyphenyl)-5-oxo-pyrrolidine-2-carboxylic acid (2-trimethylsilanylethoxy)amide (95 mg, 0.22 mmol) in methylene chloride was added boron trifluoride etherate (0.86 μL, 0.68 mmol). The mixture was stirred at room temperature for 75 minutes. During this period the suspended solid dissolved completely and the product precipitated. The mixture was quenched by addition of saturated aqueous NH4Cl solution. The title compound was collected by filtration, washing well with ethyl acetate and water, and dried. The yield was 56 mg (78%).

Workup

  1. dissolutionDuring this period the suspended solid dissolved completely
  2. customthe product precipitated
  3. customThe mixture was quenched by addition of saturated aqueous NH4Cl solution
  4. filtrationThe title compound was collected by filtration
  5. washwashing well with ethyl acetate and water
  6. customdried

Sources & evidence

ORD record
ord-a7019faf8bac4ea48aa09f0f13c0de85
Source dataset
uspto-grants-2000_09
Patent number
US06114361

Reaction notes

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