Propanedioyl dichloride → tert-butyl (2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetate

HRID 1375354노트

반응식

HRID 1375354 반응식
[NH:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](Cl)(=[O:28])[CH2:24][C:25](Cl)=[O:26]>C1COCC1>[O:26]=[C:25]1[N:14]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:23](=[O:28])[CH2:24]1

참가 물질

4

반응물 2

HCID 74269Propanedioyl dichlorideHCID 69425039tert-butyl N-(2-anilinophenyl)glycinate

생성물 1

HCID 86602389tert-butyl (2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To 100 mL of THF at 0° C. was added dropwise over 20 min simultaneously a solution of the tert-butyl N-(2-anilinophenyl)glycinate (9.5 g, 31.8 mM) in 100 mL of THF and solution of malonyl dichloride (5.38 mL, 38.21 mM) in 100 mL of THF. The resulting solution was stirred at RT for 20 h and the solvent removed in vacuo. The resultant material was purified by silica gel flash column chromatography using hexanes/EtOAc 6/14 and the combined filtrates evaporated in vacuo to give 10.2 g of product. 1H NMR (DMSO-d6) 1.40 (s, 9H), 3.19 (d, J=12 Hz, 1H), 3.69 (d, J=12 Hz, 1H), 4.55 (d, J=17 Hz, 1H), 4.71 (d, J=17 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 7.20 (t, J=8 Hz, 1H), 7.33 (m, 4H), 7.46 (m, 3H).

후처리

  1. customthe solvent removed in vacuo
  2. customThe resultant material was purified by silica gel flash column chromatography
  3. customthe combined filtrates evaporated in vacuo

출처 및 근거

ORD 기록
ord-678afc13401744dc8b7cabd8de2e9a1e
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169773B2

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