HCID 57995587, compound → HCID 57995513, compound

HRID 385363Notes

Reaction equation

HRID 385363 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:9]([N+:18]([O-])=O)=[C:8]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH:7]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:7]=[C:8]([O:21][CH2:22][C:23]([F:25])([F:24])[F:26])[C:9]([NH2:18])=[C:10]([O:12][CH2:13][C:14]([F:16])([F:17])[F:15])[CH:11]=1)[CH3:2]

Participants

4

Reactant 1

HCID 57995587HCID 57995587, compound

Product 1

HCID 57995513HCID 57995513, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[4-Nitro-3,5-bis-(2,2,2-trifluoro-ethoxy)-phenyl]-acetic acid ethyl ester (10.0 g, 24.7 mmol) was dissolved in EtOH (200 mL) and hydrogenated at 50 psi, 25° C. for 16 h in the presence of Pd—C catalyst (10%, 1 g). The catalyst was filtered off and the solvent evaporated to give a crude brown oil, which was purified by silica gel gradient column chromatography by use of Heptane-EtOAc to give [4-amino-3,5-bis-(2,2,2-trifluoro-ethoxy)-phenyl]-acetic acid ethyl ester as a yellow oil (8.3 g, 90%). 1H NMR (300 MHz, CDCl3/TMS): δ 6.52 (s, 2H), 4.37 (q, J=8.0 Hz, 4H), 4.14 (q, J=7.2 Hz, 2H), 3.90 (br s, 2H), 3.48 (s, 2H), 1.25 (t, J=7.2 Hz, 3H). 13C NMR (75 MHz, CDCl3/TMS): δ 171.4, 145.0, 126.3, 123.2, (q, 1JCF=277.6 Hz), 122.6, 110.0, 109.8 (two signals), 66.8 (q, 2JCF=35.5 Hz), 61.0, 41.0, 14.2.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. customto give a crude brown oil, which
  4. customwas purified by silica gel gradient column chromatography by use of Heptane-EtOAc

Sources & evidence

ORD record
ord-0eff7ee3e6424a7182921db55a4d52eb
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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