Boron trifluoride → HCID 57304755, compound

HRID 1611648Notes

Reaction equation

HRID 1611648 reaction equation
[C:1]([NH:6][C@H:7]([C:10]([OH:12])=[O:11])[CH2:8][SH:9])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:13]1([C:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(F)(F)F.C([O-])(=O)C.[Na+]>CCOCC.O.C(O)(=O)C>[C:1]([NH:6][C@H:7]([C:10]([OH:12])=[O:11])[CH2:8][S:9][C:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 6356Boron trifluorideHCID 6457TriphenylcarbinolHCID 130211N-Isobutyrylcysteine2×HCID 517045Sodium Acetate

Product 1

HCID 57304755HCID 57304755, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

This compound was synthesized by adapting, to N-isobutyryl-L-cysteine, the tritylation method described by K.-Y. Zee-Cheng and C. C. Cheng, J. Med. Chem., 1970, 13, 414-418. A suspension comprising 4.1 g (21.5 mmol) of N-isobutyryl-L-cysteine [(prepared according to H. Brückner et al., J. Chromatogr., 1989, 476, 73-82), ([α]D20=+84° (c 1, CHCl3))], 5.6 g (21.5 mmol) of triphenylmethanol and 16 ml of glacial acetic acid is stirred at ambient temperature. 4.1 ml (32.2 mmol) of BF3 etherate are added dropwise to the mixture while maintaining the temperature at 20-25° C. After stirring for 3 h, the brown solution obtained is subsequently cooled to 0° C. and then 70 ml of an aqueous sodium acetate solution and 140 ml of water are added. At the end of the additions, the reaction mixture sets solid in the form of a gel. This mixture is left overnight at 0° C. and then 150 ml of ice-cold water and 120 ml of ether are subsequently added with vigorous stirring. The ethereal phase is separated by settling and the aqueous waste liquors are washed with 4×80 ml of ether. The organic phases are combined, washed with 4×60 ml of ice-cold water, dried over sodium sulfate, filtered and evaporated to dryness under vacuum. The crude product obtained is purified by washing successively with hexane (5×50 ml) to provide 13 in the form of a gum which is homogeneous by TLC with a yield of 81%. Rf (CH2Cl2/MeOH/AcOH, 9.4/0.6/0.07): 0.53. [α]D20=+21.4° (c 1.12, CHCl3).

Workup

  1. customThis compound was synthesized
  2. temperaturewhile maintaining the temperature at 20-25° C
  3. stirringAfter stirring for 3 h
  4. customthe brown solution obtained
  5. temperatureis subsequently cooled to 0° C.
  6. customThe ethereal phase is separated
  7. washthe aqueous waste liquors are washed with 4×80 ml of ether
  8. washwashed with 4×60 ml of ice-cold water
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated to dryness under vacuum
  12. customThe crude product obtained
  13. customis purified
  14. washby washing successively with hexane (5×50 ml)

Sources & evidence

ORD record
ord-0d838c3925464a9193cb33b17e7781ca
Source dataset
uspto-grants-2006_01
Patent number
US06989372B1

Reaction notes

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