Acetic Acid → HCID 86596000, compound

HRID 547276Notes

Reaction equation

HRID 547276 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][NH:9][CH2:10][C:11]1[C:12]([CH2:20][CH3:21])=[N:13][C:14]([C:17](=O)[CH3:18])=[CH:15][CH:16]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:24]1[CH:32]=[CH:31][C:27]([CH2:28][O:29][NH2:30])=[CH:26][C:25]=1[C:33]([F:36])([F:35])[F:34].[C:37](O)(=O)[CH3:38]>CO>[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][NH:9][CH2:10][C:11]1[C:12]([CH2:20][CH3:21])=[N:13][C:14]([C:17](=[N:30][O:29][CH2:28][C:27]2[CH:31]=[CH:32][C:24]([CH:38]3[CH2:37][CH2:15][CH2:16][CH2:11][CH2:10]3)=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:26]=2)[CH3:18])=[CH:15][CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67189157O-(4-chloro-3-trifluoromethyl-benzyl)-hydroxylamineHCID 67191845HCID 67191845, compound

Product 1

HCID 86596000HCID 86596000, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[(6-acetyl-2-ethyl-pyridin-3-ylmethyl)-amino]-propionic acid tert-butyl ester (1 eq) in methanol is added O-(4-chloro-3-trifluoromethyl-benzyl)-hydroxylamine (1 eq) followed by the addition of acetic acid (0.05 eq). The mixture is stirred at room temperature for 5 hours. After concentration, the residue is purified by column chromatography to give 3-({6-[1-(4-cyclohexyl-3-trifluoromethyl-benzyloxyimino)-ethyl]-2-ethyl-pyridin-3-ylmethyl}-amino)-propionic acid tert-butyl ester. MS: (ES+) 562.3 (M+1)+. The tert-butyl group is subsequently removed by treatment with TFA/DCM (1/1) at room temperature. The final compound 3-({6-[1-(4-cyclohexyl-3-trifluoromethyl-benzyloxyimino)-ethyl]-2-ethyl-pyridin-3-ylmethyl}-amino)-propionic acid is purified by preparative LCMS. 1H NMR (400 MHz, CD3OD) δ 1.30-1.62 (m, 8H), 1.72-1.91 (m, 5H), 2.36 (s, 3H), 2.78 (t, 2H), 2.94 (m, 3H), 3.37 (t, 2H), 4.42 (s, 2H), 5.29 (s, 2H), 7.51-7.80 (m, 5H). MS: (ES+): 506.3 (M+1)+.

Workup

  1. concentrationAfter concentration
  2. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-3ad63fefedfd41819641a53faa74f213
Source dataset
uspto-grants-2011_05
Patent number
US07939519B2

Reaction notes

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