Triethylamine → 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamide

HRID 502071Notes

Reaction equation

HRID 502071 reaction equation
[CH2:1]([C:3]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[C:23]([CH3:30])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].Cl.NO.[CH3:34]CN=C=NCCCN(C)C.C1C=C[C:48]2[N:53]([OH:54])N=NC=2C=1.CCN(CC)CC>CCOC(C)=O.CN(C=O)C>[CH2:1]([C:3]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:53]([O:54][CH3:34])[CH3:48])=[O:27])=[C:23]([CH3:30])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:17])([CH3:16])[CH3:18])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 443297Hydroxyamine hydrochlorideHCID 103643684-{1-[4-(3,3-Dimethyl-2-hydroxybutoxy)-3-methylphenyl]-1-ethylpropyl}-2-methylbenzoic acid

Product 1

HCID 577634414-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamideYield 81.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of enantiomer 1 of 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid (1.11 g, 2.69 mmol) and DMF (5 mL) is added hydroxylamine hydrochloride (0.29 g, 2.96 mmol), EDCI (0.57 g, 2.96 mmol), HOBt (0.40 g, 2.96 mmol), and NEt3 (1.65 mL, 11.84 mmol). The mixture is stirred at ambient temperature overnight, diluted with EtOAc (40 mL), washed with 1M HCl (40 mL), water (40 mL), brine (40 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (110%-40% EtOAc gradient) to furnish the title compound (1.0 g, 2.19 mmol, 81%).

Workup

  1. washwashed with 1M HCl (40 mL), water (40 mL), brine (40 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by ISCO (110%-40% EtOAc gradient)

Sources & evidence

ORD record
ord-5781ac4b13e643b7b06879d3abbec947
Source dataset
uspto-grants-2010_08
Patent number
US07772425B2

Reaction notes

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