Trifluoroacetic acid → HCID 68620201, compound

HRID 1433771Notes

Reaction equation

HRID 1433771 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:16](=[O:26])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[F:25])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:16]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[F:25])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68620469HCID 68620469, compound

Product 1

HCID 68620201HCID 68620201, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-[1-(2-fluoro-4-iodo-phenylcarbamoyl)-2-pyridin-2-yl-ethyl]-carbamic acid tert-butyl ester (1.2 g, 2.47 mmol) in dichloromethane (5 mL) at 0° C. was added trifluoroacetic acid (5 mL) and the mixture stirred at 0° C. for 1 hour. The reaction mixture was concentrated in vacuo and the residue suspended in ice cold water. The aqueous suspension was neutralized with saturated aqueous sodium carbonate solution to basic then extracted with dichloromethane (three times). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography over silica gel gradient eluted from 100% hexane up to 100% ethyl acetate in 40 minutes. Concentration of the product containing fractions gave (S)-2-amino-N-(2-fluoro-4-iodo-phenyl)-3-pyridin-2-yl-propionamide as a yellow solid (806 mg, 85%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthen extracted with dichloromethane (three times)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography over silica gel gradient
  7. washeluted from 100% hexane up to 100% ethyl acetate in 40 minutes
  8. additionConcentration of the product containing fractions

Sources & evidence

ORD record
ord-6b3c5b64826c4407a3ea2ecbf377d60d
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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