L-Lysine → HCID 178419118, compound

HRID 1271524Notes

Reaction equation

HRID 1271524 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[BH:11]1[CH:16]2[CH2:17][CH2:18][CH2:19][CH:12]1[CH2:13][CH2:14][CH2:15]2>CO.O1CCCC1>[BH:11]1[CH:16]2[CH2:17][CH2:18][CH2:19][CH:12]1[CH2:13][CH2:14][CH2:15]2.[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

5

Reactant 2

HCID 5962L-LysineHCID 789669-Borabicyclo(3.3.1)nonane

Product 1

HCID 178419118HCID 178419118, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A sample of lysine, 1, (1 eq) is stirred in MeOH (0.03M solution) at ambient temperature. An aliquot of a solution of 9-borobicyclononane (9-BBN) (1 eq), 2, in tetrahydrofuran (THF) is introduced by syringe, and the cloudy reaction mixture is stirred under refluxing conditions (˜50° C.) over 1 hour to give a clear colorless solution. The volatile organic solvents are removed under reduced pressure to give a solid that is then redissolved in warm (˜40° C.) THF and filtered to provide a colorless solution. The solution is filtered and the volatiles are removed in vacuo to afford 9-BBN-lysine, 3, as an off white solid, which is then washed with pentanes, dried in vacuo and used without further purification.

Workup

  1. customthe cloudy reaction mixture
  2. customto give a clear colorless solution
  3. customThe volatile organic solvents are removed under reduced pressure
  4. customto give a solid
  5. dissolutionthat is then redissolved
  6. filtrationfiltered
  7. customto provide a colorless solution
  8. filtrationThe solution is filtered
  9. customthe volatiles are removed in vacuo

Sources & evidence

ORD record
ord-0e95d2dd85004585a48e394da6397a8b
Source dataset
uspto-grants-2007_04
Patent number
US07205385B2

Reaction notes

Loading…