Trifluoroacetic acid → HCID 61148470, compound

HRID 565250Notes

Reaction equation

HRID 565250 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:23])[C@@H:10]([NH:15]C(OC(C)(C)C)=O)[C:11]([CH3:14])([CH3:13])[CH3:12].FC(F)(F)C(O)=O>ClCCl.C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:23])[C@@H:10]([NH2:15])[C:11]([CH3:12])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70237877Carbamic acid, [(1S)-2,2-dimethyl-1-[[(2-pyridinylmethyl)amino]carbonyl]propyl]-, 1,1-dimethylethyl ester

Product 1

HCID 61148470HCID 61148470, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid 2-pyridylmethylamide (16 g, 50 mmol) in dichloromethane (25 mL) cooled at 0° C. is added trifluoroacetic acid (150 mL). The resulting solution is allowed to warm to 25° C. and is stirred for 18 h. The reaction mixture is diluted with toluene, concentrated, brought to pH=10 with 2 M sodium hydroxide, and extracted with 3:1 dichloromethane/isopropanol (200 mL). The organic layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (2S)-2-Amino-3,3-dimethylbutanoic acid 2-pyridylmethylamide (11 g, 100% yield) as a white solid.

Workup

  1. concentrationconcentrated
  2. extractionextracted with 3:1 dichloromethane/isopropanol (200 mL)
  3. washThe organic layer is washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d0e143eb0c948da92f237e62b8c8100
Source dataset
uspto-grants-2001_01
Patent number
US06172064B2

Reaction notes

Loading…