Boron trifluoride → HCID 11435057, compound

HRID 1291784Notes

Reaction equation

HRID 1291784 reaction equation
B(F)(F)F.C([NH:12][C@@H:13]([CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH:14](O)[CH2:15][Si](C)(C)C)(OC(C)(C)C)=O.C(=O)([O-])[O-].[Na+].[Na+]>CCOCC.C(Cl)Cl>[CH:22]1([CH2:21][C@H:13]([NH2:12])[CH:14]=[CH2:15])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 6356Boron trifluorideHCID 10340Sodium CarbonateHCID 131720659HCID 131720659, compound

Product 1

HCID 11435057HCID 11435057, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

42.2 ml (336 mmol) of an approximately 48% solution of boron trifluoride in ether are added at 5° C. to a solution of 23.1 g (67.2 mmol) of 3(S)-(Boc-amino)-2(R,S)-hydroxy-4-cyclohexyl-1-trimethylsilyl-butane in 460 ml of methylene chloride. The reaction mixture is then stirred for 6 h at RT and 3M sodium carbonate solution is added. The aqueous phase is removed and extracted twice with methylene chloride. The organic extracts are washed with brine, dried over sodium sulfate and concentrated by evaporation. The title product is further used without additional purification.

Workup

  1. customThe aqueous phase is removed
  2. extractionextracted twice with methylene chloride
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe title product is further used without additional purification

Sources & evidence

ORD record
ord-c42e091fd7004b799837c1d550cc69fe
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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