N,N-Diethyl-1-propyn-1-amine → p-Nitrobenzyl 2-(5-diethylamino-4-methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylate

HRID 1762676

반응식

HRID 1762676 반응식
[N:1]([C:4]1[CH2:5][C@@H:6]2[CH2:23][C:22](=[O:24])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10])=[N+:2]=[N-:3].[CH2:25]([N:27]([CH2:31][CH3:32])[C:28]#[C:29][CH3:30])[CH3:26]>ClCCl>[CH2:25]([N:27]([CH2:31][CH3:32])[C:28]1[N:1]([C:4]2[CH2:5][C@@H:6]3[CH2:23][C:22](=[O:24])[N:7]3[C:8]=2[C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)=[O:10])[N:2]=[N:3][C:29]=1[CH3:30])[CH3:26]

참가 물질

4

반응물 2

HCID 77909N,N-Diethyl-1-propyn-1-amineHCID 131715741p-Nitrobenzyl 2-azidocarbapen-2-em-3-carboxylate

생성물 1

HCID 131715755p-Nitrobenzyl 2-(5-diethylamino-4-methyl-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylate수율 15.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A stirred, 0° C. solution of p-nitrobenzyl 2-azido-carbapen-2-em-3-carboxylate (5.9 mg, 18 micromol) in dry dichloromethane (0.30 ml) was treated with 1-diethylaminopropyne (2.5 microliter, 2.0 mg, 18 micromol). After 1.25 hours the mixture was filtered through a 6 cm×4 mm column of florisil and the eluate was evaporated under vacuum. The residue was chromatographed on one 5 cm×20 cm 250 micron silica gel thin layer chromatography plate developed with 5:1 (v/v) dichloromethane-ethyl acetate, and the band centered at Rf 0.30 was eluted with ethyl acetate. The elutate was evaporated under vacuum to provide 1.2 mg (15%) p-nitrobenzyl 2-(5-diethylamino-4-methyl-1,2,3-triazol-1-yl)carbapen-2-em-3-carboxylate; IR (CH2Cl2): 1785, 1730 cm-1 ; NMR (CDCl3): δ 0.92 t (J=7 Hz, 6H), 2.30 s (3H), 2.97 q (J=7 Hz, 4H), 3.18 dd (J1 =4 Hz, J2 =17 Hz, 1H), 3.24 dd (J1 =10 Hz, J2 =18 Hz, 1H), 3.40 dd (J1 =8 Hz, J2 =18 Hz, 1H), 3.65 dd (J1 =6 Hz, J2 =17 Hz, 1H), 4.25 m (1H), 5.22 d (J=14 Hz, 1H), 5.32 d (J=14 Hz, 1H), 7.45 d (J=9 Hz, 2H), 8.22 d (J=9 Hz); MS (m/e): 440, 414, 412, 398, 384, 369, 357, 355, 341, 333.

후처리

  1. filtrationAfter 1.25 hours the mixture was filtered through a 6 cm×4 mm column of florisil
  2. customthe eluate was evaporated under vacuum
  3. customThe residue was chromatographed on one 5 cm×20 cm 250 micron silica gel thin layer chromatography plate
  4. washwas eluted with ethyl acetate
  5. customThe elutate was evaporated under vacuum

출처 및 근거

ORD 기록
ord-dfe57ac97a1c4fcab2da4fde97ac3c13
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04833167

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