Trifluoroacetic acid → N-Allyl-N-benzyl-2-(benzylamino)acetamide

HRID 2264835Notes

Reaction equation

HRID 2264835 reaction equation
C(O)(C(F)(F)F)=O.[O:8]=[C:9]([N:26]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:27][CH:28]=[CH2:29])[CH2:10][N:11]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C(=O)OC(C)(C)C>ClCCl>[C:31]1([CH2:30][N:26]([CH2:27][CH:28]=[CH2:29])[C:9](=[O:8])[CH2:10][NH:11][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59596676tert-Butyl (2-(allyl(benzyl)amino)-2-oxoethyl)(benzyl)carbamate

Product 1

HCID 59596664N-Allyl-N-benzyl-2-(benzylamino)acetamideYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (3 ml) was added dropwise to a solution of 1,1-dimethylethyl {2-oxo-2-[(phenylmethyl)(2-propen-1-yl)amino]ethyl}(phenylmethyl)carbamate (D89, 1.18 g, 3 mmol) in dry dichloromethane (12 ml) at 0° C. After stirring at room temperature for 3 h the solvent was evaporated and the residue purified via SCX cartridge to give the title compound (880 mg, quant.) as a clear oil. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.4-7.2 (m, 10H), 5.9-5.6 (m, 1H), 5.2-5.0 (m, 2H), 4.6, 4.4 (s, 2H), 4.1-3.7 (m, 4H), 3.5 (s, 2H), 2.4 (bs, 1H).

Workup

  1. customwas evaporated
  2. customthe residue purified via SCX cartridge

Sources & evidence

ORD record
ord-514fe6e9f2444e059fcee0fbe81f5c87
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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