Triphenylphosphine → (2S,4S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-4-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate

HRID 516173노트

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HRID 516173 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:34][C:35]1[C:36]2[C:43]([I:44])=[CH:42][NH:41][C:37]=2[N:38]=[CH:39][N:40]=1.[Si:45]([O:62][CH2:63][C@@H:64]1[CH2:68][C@@H:67](O)[CH2:66][N:65]1[C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])([C:58]([CH3:61])([CH3:60])[CH3:59])([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C1COCC1.O.C(OCC)(=O)C>[Si:45]([O:62][CH2:63][C@@H:64]1[CH2:68][C@H:67]([N:41]2[C:37]3[N:38]=[CH:39][N:40]=[C:35]([Cl:34])[C:36]=3[C:43]([I:44])=[CH:42]2)[CH2:66][N:65]1[C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])([C:58]([CH3:60])([CH3:61])[CH3:59])([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 148092816-Chloro-7-iodo-7-deazapurineHCID 69332404HCID 69332404, 화합물

생성물 1

HCID 89870881(2S,4S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-4-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A solution of triphenylphosphine (443 mg) in THF (25 ml) was cooled to 0° C., and DIAD (340 μl) was added thereto dropwise. The reaction mixture was stirred at 0° C. for 1 hour. 4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (363 mg) and the (2S,4R)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-4-hydroxypyrrolidine-1-carboxylate (651.6 mg) obtained in Example 28 (Step 1) were added thereto, and stirred at room temperature overnight. Ethyl acetate and water were added to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a light-yellow, amorphous substance (400 mg). m/z [M+H]+ 718.5

후처리

  1. stirringstirred at room temperature overnight
  2. customto separate the organic layer
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-5cbee11f616e4b389d2b3731120db7a7
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108973B2

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