5,5,5-trifluoropentanoic Acid → (S)-methyl 2-(5,5,5-trifluoro-N-methylpentanamido)hex-5-enoate

HRID 501675Notes

Reaction equation

HRID 501675 reaction equation
[F:1][C:2]([F:10])([F:9])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=O.Cl.[CH3:12][NH:13][C@@H:14]([CH2:19][CH2:20][CH:21]=[CH2:22])[C:15]([O:17][CH3:18])=[O:16]>>[F:9][C:2]([F:1])([F:10])[CH2:3][CH2:4][CH2:5][C:6]([N:13]([C@@H:14]([CH2:19][CH2:20][CH:21]=[CH2:22])[C:15]([O:17][CH3:18])=[O:16])[CH3:12])=[O:8]

Participants

3

Reactant 2

HCID 27824465,5,5-trifluoropentanoic AcidHCID 86622315(S)-methyl 2-(methylamino)hex-5-enoate hydrochloride

Product 1

HCID 86622316(S)-methyl 2-(5,5,5-trifluoro-N-methylpentanamido)hex-5-enoateYield 65%

Procedure

Step L (1): 5,5,5-Trifluoropentanoic acid and (S)-methyl 2-(methylamino)hex-5-enoate hydrochloride from Step K (2) were coupled according to the conditions described in Step A (1). The crude reaction products were purified by silica-gel column chromatography to give 276 mg (65% yield) of (S)-methyl 2-(5,5,5-trifluoro-N-methylpentanamido)hex-5-enoate. LC-MS (M+H)+=296.3; 1H NMR (500 MHz, CDCl3) δ ppm 1.73-1.83 (m, 1H) 1.84-2.25 (m, 7H) 2.37-2.52 (m, 2H) 2.78-2.96 (m, 3H) 3.66-3.75 (m, 3H) 4.94-5.09 (m, 2H) 5.17 (dd, J=10.53, 4.73 Hz, 1H) 5.70-5.84 (m, J=6.71 Hz, 1H).

Workup

  1. customThe crude reaction products
  2. customwere purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-9d059070e54c4bea9549051e929574ce
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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