Ethanamine, 2,2,2-trifluoro- → HCID 52775552, compound

HRID 587768Notes

Reaction equation

HRID 587768 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.[F:27][C:28]([F:32])([F:31])[CH2:29][NH2:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:13][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:14])[C:10](=[O:12])[NH:30][CH2:29][C:28]([F:32])([F:31])[F:27]

Participants

6

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 52775552HCID 52775552, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-((tert-butoxycarbonyl)amino)-2-methylpropanoic acid (4.58 g, 22.6 mmol) in methylene chloride (50 mL) was added EDC HCl (4.75 g, 24.8 mmol) followed by 2,2,2-trifluoroethylamine (2.67 g, 27.0 mmol) and DMAP (3.03 g, 24.8 mmol). The reaction mixture was stirred at ambient temperature for 18 h, then washed with aqueous 5% NaHSO4 (2×), aqueous 10% HCl (1×) and aqueous saturated NaHCO3 (2×). The organic phase was dried (MgSO4) and concentrated in vacuo to afford the title compound as a white solid (2.97 g, 46%).

Workup

  1. washwashed with aqueous 5% NaHSO4 (2×), aqueous 10% HCl (1×) and aqueous saturated NaHCO3 (2×)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c2a183acbd2424cb6eea6c3cfb7e773
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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