Sodium Hydroxide → [(4S,5R)-2-Oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]acetic acid

HRID 1762167ノート

反応式

HRID 1762167 の反応式
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[N:8]2[CH2:19][C:20]([O:22]CC)=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1.O>[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[N:8]2[CH2:19][C:20]([OH:22])=[O:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 674151183-Oxazolidineacetic acid, 2-oxo-4,5-diphenyl-, ethyl ester, cis-

生成物 1

HCID 58430307[(4S,5R)-2-Oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]acetic acid収率 78.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl (4,5-cis-diphenyl-2-oxo-3-oxazolidinyl)acetate (40.6 g, 125 mmol) was dissolved in tetrahydrofuran (100 ml) and a solution of sodium hydroxide (6 g, 150 mmol) in water (40 ml) was added thereto. The mixture was stirred at room temperature for 15 minutes. To the homogeneous solution was added water (150 ml) and the mixture was washed twice with diisopropyl ether (20 ml). The aqueous layer was adjusted to pH 2 with a 10-fold dilution of concentrated hydrochloric acid and extracted with ethyl acetate. The extract was dried over magnesium sulfate and filtered. The filtrate was concentratred and the residue was recrystallized from methylenechloride-n-hexane mixture to give the title compound (29.1 g) as white crystals.

後処理

  1. washthe mixture was washed twice with diisopropyl ether (20 ml)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe residue was recrystallized from methylenechloride-n-hexane mixture

出典と根拠

ORDレコード
ord-9d1d13677cfb427a82806909097c676f
出典データセット
uspto-grants-1989_05
特許番号
US04831026

反応ノート

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