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(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one → 5-((R)-2-{2-[4-((S)-2-hydroxy-2-phenylethylamino)phenyl]-ethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl)-8-benzyloxy-1H-quinolin-2-one

HRID 2425506
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HRID 2425506 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[OH:13])=[CH:6][CH:5]=1.[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]([C@@H:39]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[CH2:40]Br)=[C:32]2[C:37]=1[NH:36][C:35](=[O:38])[CH:34]=[CH:33]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CS(C)=O>[OH:13][C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][NH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][CH2:40][C@@H:39]([C:31]2[CH:30]=[CH:29][C:28]([O:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:37]3[C:32]=2[CH:33]=[CH:34][C:35](=[O:38])[NH:36]3)[O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])=[CH:5][CH:6]=1
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참가 물질

4

반응물 2

HCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 22986856(S)-2-[4-(2-aminoethyl)phenylamino]-1-phenylethanol

생성물 1

HCID 672471095-((R)-2-{2-[4-((S)-2-hydroxy-2-phenylethylamino)phenyl]-ethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl)-8-benzyloxy-1H-quinolin-2-one

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
120 °C

실험 절차

Under nitrogen, (S)-2-[4-(2-aminoethyl)-phenylamino]-1-phenylethanol (1.7 g, 6.6 mmol) and 8-benzyloxy-5-[(R)-2-bromo-1-(tert-butyldimethylsilanyloxy)ethyl]-1H-quinolin-2-one (1.5 g, 3.1 mmol) were treated with dimethyl sulfoxide (4.0 mL) and heated to 120° C. for 40 minutes. The mixture was cooled slowly to room temperature and partitioned between water and ethyl acetate (after removal of some insoluble gummy residue by decantation). The organics were washed with 0.9 M sodium acetate/acetic acid, saturated sodium hydrogen carbonate and saturated sodium chloride, dried over sodium sulfate and evaporated to dryness. The title intermediate was used without further purification.

후처리

  1. temperatureThe mixture was cooled slowly to room temperature
  2. custompartitioned between water and ethyl acetate (
  3. customafter removal of some insoluble gummy residue by decantation)
  4. washThe organics were washed with 0.9 M sodium acetate/acetic acid, saturated sodium hydrogen carbonate and saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe title intermediate was used without further purification

출처 및 근거

ORD 기록
ord-93ef6b169eae49e082d208d93e02d688
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07964730B2

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