Carbon tetrabromide → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-bromopropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

HRID 505261노트

반응식

HRID 505261 반응식
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[CH:30](O)[CH2:31][CH3:32])[C@H:14]2[CH3:34])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(Br)(Br)(Br)[Br:38].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[CH:30]([Br:38])[CH2:31][CH3:32])[C@H:14]2[CH3:34])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86628753(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-hydroxypropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

생성물 1

HCID 57617882(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-bromopropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a 0° C. solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-hydroxypropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (212.4 mg, 0.402 mmol) in CH2Cl2 (5 mL) was added CBr4 (333 mg, 1.00 mmol) and a solution of PPh3 (250 mg, 0.956 mmol) in CH2Cl2 (5 mL). The reaction was allowed to warm to room temperature. After 72 hours, the reaction was concentrated and purified by flash chromatography (10 to 50% EtOAc/hexanes) to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(1-bromopropyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. LCMS=594.1 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.89-7.46 (m, 6H), 5.81-5.69 (m, 1H), 5.25-4.97 (m, 2H), 4.36-3.83 (m, 2H), 2.46-2.34 (m, 1H), 2.25-2.14 (m, 1H), 1.29-1.01 (m, 3H), 0.83-0.78 (m, 3H).

후처리

  1. concentrationthe reaction was concentrated
  2. custompurified by flash chromatography (10 to 50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-368793ebc0434341abbb09c248a856b8
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781426B2

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