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Sodium Carbonate → (S)-2-(3-aminophenyl)-7-methoxy-8-(3-((S)-7-methoxy-2-(4-methoxyphenyl)-5,11-dioxo-10-((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yloxy)propyloxy)-10((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

HRID 2047961
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인쇄 미리보기

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HRID 2047961 반응식
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH2:20][C@@H:21]3[N:27]([CH:28]=2)[C:26](=[O:29])[C:25]2[CH:30]=[C:31]([O:72][CH3:73])[C:32]([O:34][CH2:35][CH2:36][CH2:37][O:38][C:39]4[C:69]([O:70][CH3:71])=[CH:68][C:42]5[C:43](=[O:67])[N:44]6[CH:59]=[C:58](S(C(F)(F)F)(=O)=O)[CH2:57][C@H:45]6[C:46](=[O:56])[N:47]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[C:41]=5[CH:40]=4)=[CH:33][C:24]=2[N:23]([CH2:74][O:75][CH2:76][CH2:77][Si:78]([CH3:81])([CH3:80])[CH3:79])[C:22]3=[O:82])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[NH2:1][C:2]1[CH:3]=[C:4]([C:58]2[CH2:57][C@@H:45]3[N:44]([CH:59]=2)[C:43](=[O:67])[C:42]2[CH:68]=[C:69]([O:70][CH3:71])[C:39]([O:38][CH2:37][CH2:36][CH2:35][O:34][C:32]4[C:31]([O:72][CH3:73])=[CH:30][C:25]5[C:26](=[O:29])[N:27]6[CH:28]=[C:19]([C:16]7[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=7)[CH2:20][C@H:21]6[C:22](=[O:82])[N:23]([CH2:74][O:75][CH2:76][CH2:77][Si:78]([CH3:79])([CH3:81])[CH3:80])[C:24]=5[CH:33]=4)=[CH:40][C:41]=2[N:47]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:53])([CH3:54])[CH3:55])[C:46]3=[O:56])[CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 86676188HCID 86676188, 화합물

생성물 1

HCID 86676187(S)-2-(3-aminophenyl)-7-methoxy-8-(3-((S)-7-methoxy-2-(4-methoxyphenyl)-5,11-dioxo-10-((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yloxy)propyloxy)-10((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione
수율 85%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
30 °C

실험 절차

Solid 3-aminobenzeneboronic acid (0.143 g, 0.92 mmol) was added to a solution of the mono triflate (17)(0.619 g, 0.58 mmol), sodium carbonate (195 mg, 1.84 mmol) and palladium tetrakis triphenylphosphine (26.6 mg, 0.023 mmol) in toluene (10 mL), ethanol (5 mL) and water (5 mL). The reaction mixture was allowed to stir at room temperature for overnight at 30° C. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulphate. Excess solvent was removed by rotary evaporation under reduced pressure and the resulting residue was subjected to flash column chromatography (silica gel; gradient elution EtOAc/hexane 70/3085/15). Removal of excess eluent from selected fractions afforded the desired product (0.502 g, 0.49 mmol, 85%).

후처리

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. customExcess solvent was removed by rotary evaporation under reduced pressure
  5. washthe resulting residue was subjected to flash column chromatography (silica gel; gradient elution EtOAc/hexane 70/3085/15)
  6. customRemoval of excess eluent

출처 및 근거

ORD 기록
ord-061417c24da24bd68558ad641900f4b7
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08592576B2

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