Diisopropylethylamine → 1-Boc-N-(2-propyn-1-yl)azetidine-3-carboxamide

HRID 528732ノート

反応式

HRID 528732 の反応式
[C:1]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.C[N:17](C)[CH2:18][CH2:19][CH2:20]N=C=NCC.O.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.C(N)C#C>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH:10]([C:12](=[O:14])[NH:17][CH2:18][C:19]#[CH:20])[CH2:11]1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

参加物

7

反応物 5

HCID 81531DiisopropylethylamineHCID 239041PropargylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 866671721-Boc-N-(2-propyn-1-yl)azetidine-3-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To 0.5 g (2.48 mmol) boc-azetidine-3-carboxylic acid in 5 mL DCM were added 0.52 g (2.73 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.4 g (2.98 mmol) 1-hydroxybenzotriazole hydrate and 0.9 mL (5.47 mmol) DIPEA, and the reaction was stirred at room temperature for 30 minutes. 0.19 mL (2.73 mmol) propargylamine was added and the reaction was stirred for 16 hours at room temperature. 5 mL DCM was added and the mixture was washed with 10 mL aqueous HCl (1 M), then 10 mL aqueous NaHCO3 (1 M) and 10 mL brine. The organic layer was dried over Na2SO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, heptane/EtOAc 7:3).

後処理

  1. stirringthe reaction was stirred for 16 hours at room temperature
  2. washthe mixture was washed with 10 mL aqueous HCl (1 M)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationAfter filtration and evaporation of the solvent the product
  5. customwas purified by column chromatography (silica, heptane/EtOAc 7:3)

出典と根拠

ORDレコード
ord-35d3d9d9a17d41278b9cdac0bf2ed3e9
出典データセット
uspto-grants-2016_05
特許番号
US09346816B2

反応ノート

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