Ethyl bromoacetate → [(5S*,9R*)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-yl]-acetic acid ethyl ester

HRID 489243

반응식

HRID 489243 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@:12]3([C@H:18]([C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)[CH2:17][NH:16][CH2:15]3)[N:11]([CH3:27])[C:10]2=[O:28])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:29][CH2:30][O:31][C:32]([CH2:34]Br)=[O:33].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[CH2:30]([O:31][C:32](=[O:33])[CH2:34][N:16]1[CH2:17][C@@H:18]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[C@:12]2([N:11]([CH3:27])[C:10](=[O:28])[N:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:13]2=[O:14])[CH2:15]1)[CH3:29]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 119947544-[(5S,9R)-3-(3,5-Dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrile

생성물 1

HCID 60054719[(5S*,9R*)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-yl]-acetic acid ethyl ester수율 39.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of Example 15 (100 mg, 0.24 mmol), ethyl bromo acetate (29 μl, 0.26 mmol) and K2CO3 (36.6 mg, 0.26 mmol) in toluene (2 ml) was heated to 100° C. for 5 h. After cooling to room temperature, the precipitate (unreacted starting material) was removed by filtration. The filtrate was concentrated and purified by chromatography over silica gel (eluent: DCM then acetone) to yield the above-titled compound as an oil (47.2 mg). 1H NMR (CDCl3): 7.63 (2H, d, J=8.3 Hz), 7.25-7.30 (3H, m), 6.68 (2H, d, J=1.5Hz), 4.23 (2H, q, J=7.1 Hz), 3.89 (1H, dd, J1=11.7 Hz, J2=6.3 Hz), 3.55-3.65 (2H, m), 3.3-3.5 (3H, m), 3.26 (3H, s), 3.05 (1H, d, J=10.8 Hz), 1.31 (3H, t, J=7.1 Hz).

후처리

  1. customthe precipitate (unreacted starting material) was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. custompurified by chromatography over silica gel (eluent

출처 및 근거

ORD 기록
ord-2c92a1e14eaf43bba516256cb35c60b5
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977267B2

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