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Triphenylphosphine → HCID 68313148, 화합물

HRID 1530385
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HRID 1530385 반응식
C(OC(N1CCC(C(O[C:21]2[CH:43]=[CH:42][C:24]3[C:25]4[N:29]([CH2:30][CH2:31][O:32][C:23]=3[CH:22]=2)[CH:28]=[C:27]([C:33]2[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=2)[N:26]=4)CC)CC1)=O)C1C=CC=CC=1.[C:44]([O:48][C:49]([N:51]1[CH2:57][CH2:56][CH2:55][CH:54]([CH:58]([OH:60])[CH3:59])[CH2:53][CH2:52]1)=[O:50])([CH3:47])([CH3:46])[CH3:45].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>O1CCOCC1.CCOC(C)=O>[C:44]([O:48][C:49]([N:51]1[CH2:57][CH2:56][CH2:55][CH:54]([CH:58]([O:60][C:21]2[CH:43]=[CH:42][C:24]3[C:25]4[N:29]([CH2:30][CH2:31][O:32][C:23]=3[CH:22]=2)[CH:28]=[C:27]([C:33]2[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=2)[N:26]=4)[CH3:59])[CH2:53][CH2:52]1)=[O:50])([CH3:47])([CH3:46])[CH3:45]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68312705HCID 68312705, 화합물HCID 68312905HCID 68312905, 화합물

생성물 1

HCID 68313148HCID 68313148, 화합물수율 15%

시약·촉매·용매 2

HCID 8857
Ethyl Acetate
용매
HCID 312751,4-Dioxane용매

실험 절차

To a suspension of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol from Example 4 (267 mg, 0.82 mmol), 4-(1-hydroxyethyl)azepane-1-carboxylic acid tertbutyl ester (300 mg, 1.23 mmol) and triphenylphosphine (365 mg, 1.39 mmol) in dioxane (3 mL) was added dropwise DIAD (273 ul, 1.39 mmol) and the reaction mixture was stirred at RT for 2 h. The mixture was then diluted with EtOAc and washed with aq. NaOH (1N). The aqueous phase was extracted with EtOAc (×3) and the combined organic layers were then washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in DCM followed by Si-PCC, gradient 0-10% MeOH in EtOAc) affording the title compound as a colorless oil (60 mg, 15%). LCMS: RT 4.08 min [M+H]+ 551.2

후처리

  1. washwashed with aq. NaOH (1N)
  2. extractionThe aqueous phase was extracted with EtOAc (×3)
  3. washthe combined organic layers were then washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in DCM followed by Si-PCC, gradient 0-10% MeOH in EtOAc)

출처 및 근거

ORD 기록
ord-802580a81d6140119489fee8d4fe39c7
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090628B2

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