Trifluoroacetic acid → HCID 22880269, compound

HRID 249909Notes

Reaction equation

HRID 249909 reaction equation
[CH2:1]([N:8]([CH3:21])[C:9](=[O:20])[C@@H:10]([NH:12]C(=O)OC(C)(C)C)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:12][C@@H:10]([CH3:11])[C:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:21])=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 28168303HCID 28168303, compound

Product 1

HCID 22880269HCID 22880269, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of (S)-tert-butyl 1-(benzyl(methyl)amino)-1-oxopropan-2-ylcarbamate (26.3 g, 0.090 mol) in CH2Cl2 (100 mL) was added TFA(100 mL) drop wise. The reaction mixture was warmed to ambient temperature. After 18.5 h, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between CH2Cl2 (250 mL) and saturated NaHCO3 (250 mL). The aqueous layer was separated and basified to pH=9-10 with 1 N NaOH and extracted again with CH2Cl2 (100 mL). The combined organic layers were washed with saturated NaHCO3 (100 mL), H2O (100 mL), brine (100 mL), dried (Na2SO4) and concentrated under reduced pressure to give (S)-2-amino-N-benzyl-N-methylpropanamide (14.7 g, 85%) as an amber oil. 1H NMR consistent.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 (250 mL) and saturated NaHCO3 (250 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted again with CH2Cl2 (100 mL)
  5. washThe combined organic layers were washed with saturated NaHCO3 (100 mL), H2O (100 mL), brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f32e753f6472458284eca1fc41a514a6
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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