Trifluoroacetic acid → 2-Amino-pentanoic acid (5-cyclopentylmethyl-isoxazol-3-yl)-amide

HRID 1353124Notes

Reaction equation

HRID 1353124 reaction equation
C(OC(=O)[NH:7][CH:8]([C:12](=[O:25])[NH:13][C:14]1[CH:18]=[C:17]([CH2:19][CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[O:16][N:15]=1)[CH2:9][CH2:10][CH3:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:20]1([CH2:19][C:17]2[O:16][N:15]=[C:14]([NH:13][C:12](=[O:25])[CH:8]([NH2:7])[CH2:9][CH2:10][CH3:11])[CH:18]=2)[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69470976[1-(5-Cyclopentylmethyl-isoxazol-3-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 860096262-Amino-pentanoic acid (5-cyclopentylmethyl-isoxazol-3-yl)-amideYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-(5-Cyclopentylmethyl-isoxazol-3-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester (14.0 mmol) was dissolved in 100 mL of anhydrous dichloromethane at rt under N2. Triflouroacetic acid (140 mmol) was added and the reaction was stirred for 18 h. The crude reaction was concentrated under reduced pressure. The residual oil was redissolved in 100 mL Et2O and washed with 100 mL 1N NaOH, followed by 100 mL aqueous saturated sodium chloride solution. The organics were then dried over Na2SO4, filtered and concentrated under reduced pressure to give 2-Amino-pentanoic acid (5-Cyclopentylmethyl-isoxazol-3-yl)-amide (11.3 mmol).

Workup

  1. customThe crude reaction
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe residual oil was redissolved in 100 mL Et2O
  4. washwashed with 100 mL 1N NaOH
  5. dry with materialThe organics were then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cde899ca411040e5b9930345b97b5d6a
Source dataset
uspto-grants-2007_05
Patent number
US07220865B2

Reaction notes

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