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Hydrochloric Acid → benzyl (2R, 4S)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate

HRID 431759
ノート
印刷プレビュー

反応式

HRID 431759 の反応式
C([O:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C@@H:7]([C:20]2[O:21][C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)[CH2:6]1)(=O)C.C[O-].[Na+].Cl>CC#N.CO>[C:25]1([C:23]2[N:24]=[C:20]([C@H:7]3[CH2:6][C@H:5]([OH:4])[CH2:9][N:8]3[C:10]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[O:21][C:22]=2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86759291benzyl (2R, 4S)-4-acetoxy-2-(4,5-diphenyloxazol-2-yl)pyrrolidine-1-carboxylate

生成物 1

HCID 86759292benzyl (2R, 4S)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate収率 72.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 6342
Acetonitrile
溶媒

実験手順

To a solution of benzyl (2R, 4S)-4-acetoxy-2-(4,5-diphenyloxazol-2-yl)pyrrolidine-1-carboxylate (1.49 g) in MeCN (15 mL) was added 28% sodium methylate in MeOH (0.72 mL) at 5° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added 1N HCl (3.8 mL) under ice-cooling, and extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogen carbonate solution, water and brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by silica gal column chromatography (hexane-EtOAc, 1:3 elution) to give benzyl (2R, 4S)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate (980.8 mg).

後処理

  1. temperaturecooling
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water, saturated sodium hydrogen carbonate solution, water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gal column chromatography (hexane-EtOAc, 1:3 elution)

出典と根拠

ORDレコード
ord-79e388c0650c44bd9f20e9d184395fb3
出典データセット
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06660759B1

反応ノート

読み込み中…

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