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Dimethylamine, hydrochloride → Tert-butyl 3-(dimethylcarbamoyl)azetidine-1-carboxylate

HRID 541145
ノート
印刷プレビュー

反応式

HRID 541145 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16][NH:17][CH3:18].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C>[CH3:16][N:17]([CH3:18])[C:12]([CH:10]1[CH2:11][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 59492610Tert-butyl 3-(dimethylcarbamoyl)azetidine-1-carboxylate収率 40%

試薬・触媒・溶媒 3

HCID 6228
Dimethylformamide
溶媒
HCID 8471Triethylamine溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Under a nitrogen atmosphere, triethylamine (1.2 ml) was added to a mixture of 1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid (0.804 g), dimethylamine hydrochloride (0.489 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.997 g), 1-hydroxybenzotriazole hydrate (0.796 g), and dimethylformamide (8 ml), and the mixture was stirred at room temperature for 3 days. To the reaction mixture was added ethyl acetate (30 ml), and the mixture was successively washed once with water, once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate and twice with water. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound (0.364 g, 40%).

後処理

  1. washthe mixture was successively washed once with water, once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate and twice with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-f42502a889a64692962b3741e86e26a9
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08871934B2

反応ノート

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