Triethylamine → Tert-butyl 3-(3-(3-cyanophenoxy)phenyl)-1-(dimethylamino)-1-oxopropan-2-ylcarbamate

HRID 449509Notes

Reaction equation

HRID 449509 reaction equation
[CH3:1][N:2]([CH3:22])[C:3](=[O:21])[CH:4]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1.[C:23]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)#[N:24].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cu+2]>[C:23]([C:25]1[CH:30]=[C:29]([CH:28]=[CH:27][CH:26]=1)[O:12][C:8]1[CH:7]=[C:6]([CH2:5][CH:4]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:3]([N:2]([CH3:1])[CH3:22])=[O:21])[CH:11]=[CH:10][CH:9]=1)#[N:24]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27343253-Cyanophenylboronic acidHCID 59496639Tert-butyl 1-(dimethylamino)-3-(3-hydroxyphenyl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 59496582Tert-butyl 3-(3-(3-cyanophenoxy)phenyl)-1-(dimethylamino)-1-oxopropan-2-ylcarbamateYield 135.7%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The tert-butyl [2-(dimethylamino)-1-(3-hydroxybenzyl)-2-oxoethyl]carbamate (0.025 g, 0.081 mmol) from Example 169, step 4, was combined with (3-cyanophenyl)boronic acid (Aldich, Cat. #513016) (0.024 g, 0.16 mmol) and triethylamine (0.022 mL, 0.16 mmol), and copper(II)diacetate (0.015 g, 0.081 mmol) in methylene chloride (1.0 mL) at r.t. The reaction was vigorously stirred exposed to the atmosphere. After stirring for 48 h. this was taken up in ethyl acetate, washed with 1N HCl, brine, dried over magnesium sulfate and concentrated under reduced pressure to give crude tert-butyl 3-(3-(3-cyanophenoxy)phenyl)-1-(dimethylamino)-1-oxopropan-2-ylcarbamate (0.045 g) as a semisolid residue. Analytical LCMS (M+H-Boc)+: m/z=310.0.

Workup

  1. stirringAfter stirring for 48 h.
  2. washwashed with 1N HCl, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fba1549ff87a48a486e7db75484c5bba
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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