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

HRID 230827Notes

Reaction equation

HRID 230827 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 128.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To mixture of enantiomer 2 of 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid (0.70 g, 1.70 mmol) and DMF (5 mL) is added hydroxylamine hydrochloride (0.18 g, 1.87 mmol), EDCI (0.33 g, 1.87 mmol), HOBt (0.23 g, 1.87 mmol), and NEt3 (0.95 mL, 6.79 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 to furnish the title compound (0.76 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

Sources & evidence

ORD record
ord-2159f28153cc496dad4240ed04190b0e
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

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