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

HRID 528732노트

반응식

HRID 528732 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-35d3d9d9a17d41278b9cdac0bf2ed3e9
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346816B2

반응 노트

불러오는 중…