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

HRID 2250819ノート

反応式

HRID 2250819 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 160554manganese(III) acetate dihydrate触媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fc95a5b2fea540de9ac4b82d826093a9
出典データセット
uspto-grants-2008_01
特許番号
US07317107B2

反応ノート

読み込み中…