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

반응식

C[CH:2]([N+:7]#[C-:8])[C:3]([O:5][CH3:6])=[O:4].[CH:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH3:6][O:5][C:3]([C@H:2]1[C@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:16][CH:8]=[N:7]1)=[O:4]

참가 물질

반응물 2

HCID 240Benzaldehyde

HCID 2734780Methyl 2-isocyanopropanoate

생성물 1

HCID 11195076trans-4-Methoxycarbonyl-5-phenyl-2-oxazoline수율 90%

실험 절차

Methyl α-methylisocyano-acetate was reacted with benzaldehyde in the presence of the same catalyst and under the same reaction conditions of those of Example 2. After the solvent was concentrated, the reaction mixture was subjected to silica-gel column chromatography to obtain trans-4-methoxycarbonyl-5- phenyl-2-oxazoline and the corresponding cis-form in a ratio of 87/13). Total yield: 90%. The optical purity of the trans-(4S,5R) form was measured in the same manner as in Example 1, which was 93% ee.

후처리

concentrationAfter the solvent was concentrated

출처 및 근거

ORD 기록: ord-5929a11caa0044a7b0ce4f88af819ad6
출처 데이터셋: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05128478

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