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Triethylamine → (4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4S)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one

HRID 20936
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HRID 20936 반응식
F[C:2]1[CH:3]=[C:4]([CH:40]=[C:41](F)[CH:42]=1)[CH2:5][C@H:6]([C:25](N1[C@@H](CC2C=CC=CC=2)COC1=O)=O)[C@@H:7]([C@H:9]1[CH2:13][C@@H:12](OCC=C)CN1C(OC(C)(C)C)=O)O.[F:44][C:45]1[CH:46]=[C:47]([CH:68]=[C:69]([F:71])[CH:70]=1)[CH2:48][C@H:49]1[C@@H:53]([CH:54]2[CH2:59][O:58][CH2:57][CH2:56][N:55]2C(OC(C)(C)C)=O)[O:52][C:51](=[O:67])[NH:50]1.FC1C=C(C=C(F)C=1)C[C@@H]([C@@H](C1COCCN1C(OC(C)(C)C)=O)O)C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:71][C:69]1[CH:68]=[C:47]([CH:46]=[C:45]([F:44])[CH:70]=1)[CH2:48][C@H:49]1[C@@H:53]([C@H:54]2[CH2:59][C@H:57]([OH:58])[CH2:56][N:55]2[CH:5]([C:4]2[CH:3]=[CH:2][CH:42]=[CH:41][CH:40]=2)[C:6]2[CH:7]=[CH:9][CH:13]=[CH:12][CH:25]=2)[O:52][C:51](=[O:67])[NH:50]1
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참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67315602tert-Butyl 3-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)morpholine-4-carboxylateHCID 67315777(2S,3S)-2-(3,5-difluorobenzyl)-3-(4-(tert-butoxycarbonyl)morpholin-3-yl)-3-hydroxypropanoic acidHCID 67316359(2R,4R)-tert-butyl 2-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)-4-(allyloxy)pyrrolidine-1-carboxylate

생성물 1

HCID 58608198(4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4S)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

Step D (5): tert-Butyl 3-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)morpholine-4-carboxylate. To a solution of (2S,3S)-2-(3,5-difluorobenzyl)-3-(4-(tert-butoxycarbonyl)morpholin-3-yl)-3-hydroxypropanoic acid (step D (4)), 1.6 g, 4. mmol) in toluene (100 mL) was added diphenylphosphoryl azide (1.65 g, 6 mmol) and triethyl amine (1.01 g, 10 mmol). This reaction mixture was stirred at 80° C. for 4 h. Ethyl acetate (500 mL) was added. The mixture was washed with sodium carbonate solution, H2O, dried over Na2SO4 and concentrated. The crude mixture was purified by silica gel Flash Chromatography (0% to 20% to 30% to 50% to 70% EtOAc/Hexane step gradient) to give 800 mg of the title compound: MS (ESI) (M−H)− 397.12.

후처리

  1. washThe mixture was washed with sodium carbonate solution, H2O
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude mixture was purified by silica gel Flash Chromatography (0% to 20% to 30% to 50% to 70% EtOAc/Hexane step gradient)

출처 및 근거

ORD 기록
ord-f65dc2f08e514655a0162d6999e02db9
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745470B2

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