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

HRID 449509ノート

反応式

HRID 449509 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-fba1549ff87a48a486e7db75484c5bba
出典データセット
uspto-grants-2013_07
特許番号
US08481732B2

反応ノート

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