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Diisopropylethylamine → tert-Butyl[6-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-propanoylpyridin-2-yl]carbamate

HRID 2088661
ノート
印刷プレビュー

反応式

HRID 2088661 の反応式
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:13]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:12][CH:11]=[C:10](Cl)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:20]([NH:27][CH2:28][CH2:29][NH2:30])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:13]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:12][CH:11]=[C:10]([NH:30][CH2:29][CH2:28][NH:27][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 57911766tert-Butyl (6-chloro-3-propanoylpyridin-2-yl)carbamate

生成物 1

HCID 57911744tert-Butyl[6-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-3-propanoylpyridin-2-yl]carbamate

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒
HCID 962
Water
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

730 mg (2.4 mmol) of tert-butyl(6-chloro-3-propanoylpyridin-2-yl)carbamate (Example 23A) were initially charged in 7 ml of DMSO, and 512 mg (3.2 mmol) of N-Boc-ethylenediamine and 640 μl (3.7 mmol) of N,N-diisopropylethylamine were added. The reaction mixture was irradiated in the microwave reactor at 90° C. for 45 min. The reaction mixture was taken up in a mixture of ethyl acetate and water. The organic phase was washed with saturated aqueous ammonium chloride solution and then with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The reaction mixture was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1). This gave 530 mg (53% of theory) of the product as a solid.

後処理

  1. customThe reaction mixture was irradiated in the microwave reactor at 90° C. for 45 min
  2. washThe organic phase was washed with saturated aqueous ammonium chloride solution
  3. dry with materialwith saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe reaction mixture was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1)

出典と根拠

ORDレコード
ord-108d0b116d324d52b67783b3813635e6
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08436003B2

反応ノート

読み込み中…

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