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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Tricyclohexylphosphine → [4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfanyl)pyrimidin-5-yl]boronic acid

HRID 1508534
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HRID 1508534 반응식
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25](Br)=[CH:24][N:23]=[C:22]([S:27][CH3:28])[N:21]=3)[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[B:32]1(B2OC(C)(C)CC(C)O2)[O:37]C(C)(C)CC(C)[O:33]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C([O-])(=O)C.[K+]>C1COCC1>[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([B:32]([OH:37])[OH:33])=[CH:24][N:23]=[C:22]([S:27][CH3:28])[N:21]=3)[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1
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참가 물질

6

반응물 4

HCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 2734616Bis(hexylene Glycolato)diboronHCID 57576287(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

생성물 1

HCID 86704623[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfanyl)pyrimidin-5-yl]boronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylsulfanyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (400 mg, 0.754 mmol), bis(hexyleneglycolato)diboron (249 mg, 0.981 mmol), tricyclohexylphosphine (85 mg, 0.302 mmol), potassium acetate (163 mg, 1.659 mmol), 1,1bis(di-tert-butylphosphino)ferrocene palladium dichloride (51.3 mg, 0.075 mmol) and THF (10 mL) were sealed in a microwave vessel and subject to microwave irradiation at 140° C. for 60 min. LCMS indicated complete consumption of starting material and formation of the desired product. The resulting crude mixture was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 50 g cartridge). The column was eluted by an EtOAc/hexanes mixture (0% to 40%). Related fractions were evaporated into a brown solid foam as the titled compound. LCMS calc.=495.09. found=495.91 (M+H)+.

후처리

  1. customsubject to microwave irradiation at 140° C. for 60 min
  2. customconsumption of starting material and formation of the desired product
  3. customThe resulting crude mixture was purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 50 g cartridge)
  4. washThe column was eluted by an EtOAc/hexanes mixture (0% to 40%)
  5. customRelated fractions were evaporated into a brown solid foam as the titled compound

출처 및 근거

ORD 기록
ord-cd8e506f4c7f4ad489c5e3fedee73cb5
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221834B2

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