4-Chlorobenzaldehyde → (3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-7-benzoxazolyl]pentan-3-ol

HRID 2250819노트

반응식

HRID 2250819 반응식
[NH2:1][C:2]1[C:3]([OH:22])=[C:4]([CH2:8][CH2:9][C@H:10]([OH:21])[C@@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Mn+3]>[Si:14]([O:13][C@@H:11]([CH3:12])[C@@H:10]([OH:21])[CH2:9][CH2:8][C:4]1[C:3]2[O:22][C:28]([C:27]3[CH:30]=[CH:31][C:24]([Cl:23])=[CH:25][CH:26]=3)=[N:1][C:2]=2[CH:7]=[CH:6][CH:5]=1)([C:17]([CH3:18])([CH3:20])[CH3:19])([CH3:16])[CH3:15]

참가 물질

5

반응물 2

HCID 77264-ChlorobenzaldehydeHCID 69103771(3S,4S)-1-(3-amino-2-hydroxyphenyl)-4-(tert-butyldimethylsilyloxy)pentan-3-ol

생성물 1

HCID 11775181(3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-7-benzoxazolyl]pentan-3-ol수율 76.3%

시약·촉매·용매 2

HCID 160554manganese(III) acetate dihydrate촉매HCID 1140Toluene용매

실험 절차

A mixture of (3S,4S)-1-(3-amino-2-hydroxyphenyl)-4-(tert-butyldimethylsilyloxy)pentan-3-ol (P0016; 445 mg) and 4-chlorobenzaldehyde (192 mg) in toluene (15 ml) was refluxed for 2 hours. And then to the resulting mixture of the Schiffs base was added manganese triacetate (733 mg) and the reaction mixture was refluxed for 1 hour. The precipitated manganese diacetate was then separated by filtration and the solvent was removed under reduced pressure. The crude product was purified by silica gel (26 g) column chromatography eluting with hexane/ethyl acetate (20:1) to give (3S,4S)-4-(tert-butyldimethylsilyloxy)-1-[2-(4-chlorophenyl)-7-benzoxazolyl]pentan-3-ol (P0012; 465 mg).

후처리

  1. temperaturewas refluxed for 2 hours
  2. additionAnd then to the resulting mixture of the Schiffs base
  3. temperaturethe reaction mixture was refluxed for 1 hour
  4. customThe precipitated manganese diacetate was then separated by filtration
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by silica gel (26 g) column chromatography
  7. washeluting with hexane/ethyl acetate (20:1)

출처 및 근거

ORD 기록
ord-fc95a5b2fea540de9ac4b82d826093a9
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07317107B2

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