4-Hydroxy-2-Methoxybenzaldehyde → HCID 20599096, 화합물

HRID 479245

반응식

HRID 479245 반응식
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:18]=2[CH3:19])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].OC1C=CC(C=O)=C(OC)C=1.CC1OC(C2C=CC=CC=2)=NC=1CCOS(C)(=O)=O.[CH2:56]([C@H:63]1[CH2:67][O:66][C:65](=[O:68])[N:64]1[C:69](=[O:74])[CH2:70][O:71][CH2:72][CH3:73])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1.B(OS(C(F)(F)F)(=O)=O)(CCCC)CCCC>>[CH2:56]([C@H:63]1[CH2:67][O:66][C:65](=[O:68])[N:64]1[C:69](=[O:74])[C@@H:70]([O:71][CH2:72][CH3:73])[C@H:5]([OH:6])[C:4]1[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:18]=2[CH3:19])=[CH:10][C:3]=1[O:2][CH3:1])[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

참가 물질

6

반응물 5

HCID 5195414-Hydroxy-2-MethoxybenzaldehydeHCID 2724243Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dibutylborinic acidHCID 105407732-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonateHCID 10825429(S)-4-Benzyl-3-(ethoxyacetyl)oxazolidin-2-oneHCID 180034922-Methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

생성물 1

HCID 20599096HCID 20599096, 화합물

실험 절차

In analogy to the procedures described in examples 11 a] to 11 c], 2-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde (prepared from 4-hydroxy-2-methoxy-benzaldehyde and methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester in analogy to the procedure described in example 114 b]) was reacted with (S)-4-benzyl-3-ethoxyacetyl-oxazolidin-2-one and nBu2BOTf to yield (S)-4-benzyl-3-((2S,3R)-2-ethoxy-3-hydroxy-3-{2-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4yl)-ethoxy]-phenyl}-propionyl)-oxazolidin-2-one (according to NMR, one of the four isomers is strongly predominating; the configuration was tentatively assigned as 2S, 3R according to Tetrahedron Asymmetry 1999, 1353). Reduction of (S)-4-benzyl-3-((2S,3R)-2-ethoxy-3-hydroxy-3-{2-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionyl)-oxazolidin-2-one with triethylsilane in trifluoroacetic acid then gave (S)-4-benzyl-3-((2S)-2-ethoxy-3-{2-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionyl)-oxazolidin-2-one. The (S)-4-benzyl-3-((2S)-2-ethoxy-3-{2-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionyl)-oxazolidin-2-one was subsequently saponified with 1N NaOH in THF to yield (2S)-2-ethoxy-3-{2-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid as colorless solid.

출처 및 근거

ORD 기록
ord-594d77aca8154d90af8990ab424be1cf
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642389B2

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