HCID 57995558, compound → 2-[4-Amino-3-(2,2,2-trifluoro-ethoxy)-phenyl]-3-cyclobutyl-propionic acid Methyl Ester

HRID 385368Notes

Reaction equation

HRID 385368 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:11]=1)[CH2:5][CH:6]1[CH2:9][CH2:8][CH2:7]1>CCO.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:11]=1)[CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 57995558HCID 57995558, compound

Product 1

HCID 579956482-[4-Amino-3-(2,2,2-trifluoro-ethoxy)-phenyl]-3-cyclobutyl-propionic acid Methyl EsterYield 103.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the 3-cyclobutyl-2-[4-nitro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-propionic acid methyl ester (15 g, 36.0 mmol) in EtOH (150 mL) was hydrogenated at 50 psi and 25° C. for 16 h in the presence of Pd—C catalyst (10%, 1.5 g). On the next day, the catalyst was filtered off and the solvent evaporated to give the crude product (12.3 g, 88%) as a yellow oil, which was used without purification for the next step. 1H NMR (300 MHz, CDCl3/TMS): δ 6.79-6.73 (m, 2H), 6.66 (d, J=8.0 Hz, 1H), 4.36 (q, J=8.3 Hz, 2H), 3.80 (br s, 2H), 3.63 (s, 3H), 3.35 (t, J=7.7 Hz, 1H), 2.20-1.86 (m, 4H), 1.85-1.70 (m, 3H), 1.67-1.51 (m, 2H). 13C NMR (75 MHz, CDCl3/TMS): δ 174.7, 146.7, 135.7, 129.1, 123.3 (d, 1JCF=277.6 Hz), 122.7, 115.4, 112.2, 66.4 (q, 1JCF=35.4 Hz), 51.9, 48.9, 40.8, 34.0, 28.3, 28.1, 18.5.

Workup

  1. filtrationOn the next day, the catalyst was filtered off
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-bc2c5c548cef4002be644f01d8df44e1
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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