Ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-glycinate → 2-(Methyl{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}amino)-propan-1-ol

HRID 2184083Notes

Reaction equation

HRID 2184083 reaction equation
[CH3:1][N:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:25])([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)[C@H:3]([C:5](OCC)=[O:6])[CH3:4].CN(C1C=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=1)CC(OCC)=O>>[CH3:1][N:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:25])([C:17]([F:20])([F:18])[F:19])[C:21]([F:23])([F:24])[F:22])=[CH:12][CH:11]=1)[CH:3]([CH3:4])[CH2:5][OH:6]

Participants

3

Reactant 2

HCID 10406140Ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-glycinateHCID 10451953ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}alaninate

Product 1

HCID 117242392-(Methyl{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}amino)-propan-1-olYield 84%

Procedure

Prepared in the manner of Example 23 except ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}alaninate was substituted for ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-glycinate. Purification by flash chromatography (4:1 hexanes/EtOAc) afforded the title compound as a pink oil (84%). 1H NMR (CDCl3) δ 7.48 (d, 2H), 6.86 (br d, 2H), 4.04 (m, 1H), 3.56 (m, 2H), 2.72 (s, 3H), 1.03 (d, 3H). Anal. Calc. C13H15NO2F6: C, 47.14; H, 4.56; N, 4.23. Found: C, 46.89; H, 4.61; N, 3.93. HRMS (MH+) Calc.: 332.1085. Found: 332.1073.

Workup

  1. customPurification by flash chromatography (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-c769c654e2b3480990641c77bf70b586
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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