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

HRID 653823

反応式

HRID 653823 の反応式
[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]

参加物

5

反応物 2

HCID 240BenzaldehydeHCID 547815Methyl isocyanoacetate

生成物 1

HCID 116153924-Methoxycarbonyl-5-phenyl-2-oxazoline収率 91%

試薬・触媒・溶媒 2

HCID 76223Silver(I) trifluoromethanesulfonate触媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5bfc7bf253714aea8cd17999663b9ac2
出典データセット
uspto-grants-1992_07
特許番号
US05128478

関連ノート

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