Ethyl Acetate → HCID 67098162, 화합물

HRID 2078643노트

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HRID 2078643 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@H:19]([OH:26])[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[OH:27][CH2:28][CH2:29][CH2:30][S:31]([NH:34][C:35]([C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][C:38]=1[O:46][CH:47]([CH3:49])[CH3:48])=[O:36])(=[O:33])=[O:32].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[OH:27][CH2:28][CH2:29][CH2:30][S:31]([NH:34][C:35]([C:37]1[CH:42]=[CH:41][C:40]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@H:19]([OH:26])[C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=2)=[CH:39][C:38]=1[O:46][CH:47]([CH3:49])[CH3:48])=[O:36])(=[O:33])=[O:32]

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 67097895HCID 67097895, 화합물HCID 67098073HCID 67098073, 화합물

생성물 1

HCID 67098162HCID 67098162, 화합물수율 21.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a solution of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (331 mg) in 1,4-dioxane (3.3 ml) were added [4-[[[(3-hydroxypropyl)sulfonyl]amino]carbonyl]-3-isopropoxyphenyl]boronic acid (325 mg), tetrakis(triphenylphosphine)palladium (91 mg) and aqueous solution of sodium carbonate (2M, 1.4 ml), and the mixture was stirred at 80° C. for 3 hours under nitrogen. The mixture was portioned into a mixture of ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/methanol=100/3) to give tert-butyl [2-[4′-[[[(3-hydroxypropyl)sulfonyl]amino]carbonyl]-3′-isopropoxy-4-biphenylyl]-ethyl][(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (108 mg).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate/methanol=100/3)

출처 및 근거

ORD 기록
ord-d5517b2ddbd14d32a7f8b96e96c2eaa8
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928264B2

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