Boron trifluoride → HCID 10034765, compound

HRID 1291766Notes

Reaction equation

HRID 1291766 reaction equation
B(F)(F)F.C([NH:12][C@@H:13]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:14](O)[CH2:15][Si](C)(C)C)(OC(C)(C)C)=O.[OH-].[Na+]>CCOCC.C(Cl)Cl>[C:22]1([CH2:21][C@H:13]([NH2:12])[CH:14]=[CH2:15])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 57112417HCID 57112417, compound

Product 1

HCID 10034765HCID 10034765, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

35.6 ml (0.28 mol) of an approximately 48% solution of boron trifluoride in ether are added at 5° C., over a period of 10 min, to a solution of 18.8 g (0.055 mol) of 3(S)-(Boc-amino)-2(R,S)-hydroxy-4-phenyl-1-trimethylsilyl-butane in 420 ml of methylene chloride. The reaction mixture is then stirred at RT for 16 h, cooled to 10°0 C. and, over a period of 20 min, 276 ml of a 4N sodium hydroxide solution are added. The aqueous phase is removed and extracted twice with 400 ml of methylene chloride each time. The combined organic extracts are washed with brine and dried over sodium sulfate. The title product is further used without additional purification. TLC Rf (C)=0.15; IR (methylene chloride) (cm-1): 3370, 3020, 2920, 1640, 1605.

Workup

  1. temperaturecooled to 10°0 C
  2. waitand, over a period of 20 min
  3. customThe aqueous phase is removed
  4. extractionextracted twice with 400 ml of methylene chloride each time
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe title product is further used without additional purification

Sources & evidence

ORD record
ord-4b1b226090ec4362a7fffb3412c83e87
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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