11-((tert-Butoxycarbonyl)amino)undecanoic acid → L-Leucine

HRID 987884Notes

Reaction equation

HRID 987884 reaction equation
[C:1](NCCCCCCCCCCC(O)=O)([O:3]C(C)(C)C)=[O:2].[CH3:22]N(C)C=O.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29]C=1>CN(C)C1C=CN=CC=1>[NH2:27][C@H:32]([C:1]([OH:3])=[O:2])[CH2:31][CH:30]([CH3:29])[CH3:22]

Participants

4

Reactant 2

HCID 422929011-((tert-Butoxycarbonyl)amino)undecanoic acidHCID 21954950Dimethylformamide pyridine

Product 1

HCID 6106L-Leucine

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

N-BOC-11-aminoundecanoic acid (Bachem, 0.60 g, 2.0 mmoles) was activated with disuccinimidylcarbonate (0.56 g, 2.2 mmoles) and 4-dimethylamino-pyridine (0.02 g, 0.2 mmoles) in 10 mL of dimethylformamide/pyridine (2/1, v/v) and reacted with the resin product from Part C for 60 minutes at room temperature. The resulting resin was separated by filtration, the N-α-BOC group was removed with trifluoroacetic acid in dichloromethane, and the resulting resin was treated with 90% hydrogen fluoride/anisole (v/v) for 60 minutes at 0° C. The hydrogen fluoride was removed by evaporation, and the product was extracted into 30% acetic acid/water and then lyophilized. The crude material was purified by reverse phase HPLC on a Waters Deltapak RPC-18 column using a linear gradient of 1% to 35% acetonitrile (0.05% trifluoroacetic acid) in water (0.05% trifluoroacetic acid) over 30 minutes at 15 mL/min, which after lyophilization, gave 84.8 mg of 98% pure (by HPLC) L-leucine, N-[[(11-amino-undecanoyl)-L-seryl]-L-lysyl]-, bis-trifluoroacetate.

Workup

  1. customv/v) and reacted with the resin product from Part C for 60 minutes at room temperature
  2. customThe resulting resin was separated by filtration
  3. customthe N-α-BOC group was removed with trifluoroacetic acid in dichloromethane
  4. additionthe resulting resin was treated with 90% hydrogen fluoride/anisole (v/v) for 60 minutes at 0° C
  5. customThe hydrogen fluoride was removed by evaporation
  6. extractionthe product was extracted into 30% acetic acid/water
  7. customThe crude material was purified by reverse phase HPLC on a Waters Deltapak RPC-18 column
  8. customover 30 minutes

Sources & evidence

ORD record
ord-9c971beaf8814b1b80a341d37e36e2cf
Source dataset
uspto-grants-2003_10
Patent number
US06632921B1

Reaction notes

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