N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamine → (4S,5R)-3-dichloroacetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine

HRID 507891노트

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HRID 507891 반응식
[Cl:1][CH:2]([Cl:24])[C:3]([N:5]1[C@H:9]([CH2:10]O)[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:23])[CH3:22])=[O:4].C(N(CC)C(F)(F)C(F)C(F)(F)[F:31])C>C(Cl)Cl>[Cl:1][CH:2]([Cl:24])[C:3]([N:5]1[C@H:9]([CH2:10][F:31])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:23])[CH3:22])=[O:4]

참가 물질

4

반응물 2

HCID 136149N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamineHCID 25176380HCID 25176380, 화합물

생성물 1

HCID 68470341(4S,5R)-3-dichloroacetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
22.5 °C

실험 절차

(4R,5R)-3-dichloroacetyl-2,2-dimethyl-4-hydroxymethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine (Compound XIIa) (81 g, 0.2050 moles) in methylene chloride (450 ml) reacts with N,N-diethyl-1,1,2,3,3,3-hexafluoro-1-propanamine (Ishikawa Reagent) (73.2 g, 0.328 moles) at 95-105° C. for 2-4 hours. Cooling to 20-25° C., quenching with 25% aqueous sodium hydroxide and water (2000 mL) and separation of the methylene chloride layer gives a solution of (4S,5R)-3-dichloroacetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine (Compound XIIIa) for use as an intermediate for the next step in the process.

후처리

  1. customquenching with 25% aqueous sodium hydroxide and water (2000 mL) and separation of the methylene chloride layer

출처 및 근거

ORD 기록
ord-cbc958a226b7434db4b1300775c2dbfd
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786329B2

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