Benzaldehyde → 4-Methoxycarbonyl-5-phenyl-2-oxazoline

HRID 653823

반응식

HRID 653823 반응식
[N+:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[C-:2].[CH:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:7][O:6][C:4]([CH:3]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:15][CH:2]=[N:1]1)=[O:5]

참가 물질

5

반응물 2

HCID 240BenzaldehydeHCID 547815Methyl isocyanoacetate

생성물 1

HCID 116153924-Methoxycarbonyl-5-phenyl-2-oxazoline수율 91%

시약·촉매·용매 2

HCID 76223Silver(I) trifluoromethanesulfonate촉매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

39/3 mg (0.55 mmole) of (S)-N-methyl-N-[3-(diethylamino) -propyl]-1-[(R)-1',2-bis(diphenylphosphino)ferrocenyl] -ethylamine and 14.1 mg (0.055 mmole) of silver trifluoromethane-sulfonate was stirred in methylene chloride (5.5 ml) at room temperature for 30 minutes, and then, 0.549 g (5.54 mmole) of methyl isocyano-acetate and 0.642 g (6.05 mmole) of benzaldehyde was added thereto and stirred for 20 hours at 25° C. in nitrogen After being distilled under conditions of 110° C./0.3 mmHg, 1.0 g of 4- methoxycarbonyl-5-phenyl-2-oxazoline (trans/cis =87/13) was obtained. Yield: 91%. The trans-form and the cis-form were separated from each other by column chromatography, and the optical purity of the transform was determined by means of 1H NMR spectroscopy with the same shift reagent Eu(dcm)3 as Example 1, which was 51% ee. After acid-hydrolysis with 6N HC1, L-threo-β-phenylserine, which is a known compound, was obtained.

후처리

  1. distillationAfter being distilled under conditions of 110° C./0.3 mmHg

출처 및 근거

ORD 기록
ord-5bfc7bf253714aea8cd17999663b9ac2
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05128478

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