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

HRID 449509노트

반응식

HRID 449509 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-fba1549ff87a48a486e7db75484c5bba
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481732B2

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