tert-Butanol → HCID 69458797, 화합물

HRID 1351963노트

반응식

HRID 1351963 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[O:12][C:11](=[O:13])[N:10]([C@H:14]([CH3:28])[CH2:15][C:16]3[C:24]4[C:19](=[C:20](C(O)=O)[CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.C([N:48]([CH2:51]C)CC)C.[Cl-].[NH4+].[C:55]([OH:59])([CH3:58])([CH3:57])[CH3:56]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[O:12][C:11](=[O:13])[N:10]([C@H:14]([CH3:28])[CH2:15][C:16]3[C:24]4[C:19](=[C:20]([NH:48][C:51](=[O:36])[O:59][C:55]([CH3:58])([CH3:57])[CH3:56])[CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 199401P,P-Diphenylphosphinic azideHCID 69458599HCID 69458599, 화합물

생성물 1

HCID 69458797HCID 69458797, 화합물수율 72%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 3-{(2R)-2-[(5R)-5-(3-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl]propyl}-1H-indole-7-carboxylic acid (504 mg, 1.26 mmol) in toluene (25 mL) and t-butyl alcohol (12.5 mL) are added diphenyl-phosphoryl azide (379 μL, 1.76 mmol) and triethylamine (245 μL, 1.76 mmol) under nitrogen atmosphere, and the mixture is stirred at room temperature for 30 minutes, and further stirred at 100° C. for 5 hours. The reaction solution is poured into a saturated aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, and dried over anhydrous sodium sulfate. The solvent is evaporated and the obtained crude product is purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1) to give the title compound (427 mg, 72%).

후처리

  1. stirringfurther stirred at 100° C. for 5 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic layer is washed with a saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is evaporated
  6. customthe obtained crude product
  7. customis purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1)

출처 및 근거

ORD 기록
ord-01ae5de52fed4a508285d4def8bb0660
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217724B2

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