Trifluoroacetic acid → HCID 22690639, compound

HRID 539009Notes

Reaction equation

HRID 539009 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][NH:8][C:9](=[O:22])[C@@H:10]([NH:14]C(=O)OC(C)(C)C)[CH:11]([CH3:13])[CH3:12])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:14][C@@H:10]([CH:11]([CH3:13])[CH3:12])[C:9]([NH:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:24][CH:23]=1)=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14774463HCID 14774463, compound

Product 1

HCID 22690639HCID 22690639, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (S)-tert-butyl 1-(4-methoxybenzylamino)-3-methyl-1-oxobutan-2-ylcarbamate (1.50 g, 4.46 mmol) in dichloromethane (15 mL) was cooled to 0° C. Trifluoroacetic acid (2 mL) was added and the mixture stirred at 0° C. for 7 hours. The reaction mixture was concentrated and the residue taken up in dichloromethane and washed with saturated aqueous NaHCO3 solution. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification of the crude material by column chromatography, eluting with 4% MeOH/dichloromethane with 0.1% NH4OH, provided (S)-2-amino-N-(4-methoxybenzyl)-3-methylbutanamide (0.770 g, 73%). LCMS (APCI+) m/z 237 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with saturated aqueous NaHCO3 solution
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the crude material by column chromatography
  7. washeluting with 4% MeOH/dichloromethane with 0.1% NH4OH

Sources & evidence

ORD record
ord-a4f8306d586343a48ca9cbb4b1b32e53
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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