Potassium Hydroxide → (2R,3S)-2-benzyl-3-hydroxysuccinic acid

HRID 1677771ノート

反応式

HRID 1677771 の反応式
[CH2:1]([C@H:8]([C@H:15]([OH:22])[C:16]([O:18]C(C)C)=[O:17])[C:9]([O:11]C(C)C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C1COCC1.O>[CH2:1]([C@H:8]([C@H:15]([OH:22])[C:16]([OH:18])=[O:17])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 14264444Diisopropyl (2R,3S)-2-benzyl-3-hydroxysuccinate

生成物 1

HCID 54300227(2R,3S)-2-benzyl-3-hydroxysuccinic acid収率 82%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Diisopropyl (2R,3S)-2-benzyl-3-hydroxysuccinate (2.90 g; 15.9 mmol; 1.0 eq.) was taken in THF (44 mL), cooled to 0° C. and was treated with KOH (3.17 g, 56.4 mmol) in water (14.5 mL). The resulting mixture was stirred at RT for 48 h. THF was removed and the residue was taken in water. The aqueous layer was washed with ether (100 mL) and was acidified with an aqueous solution of HCl (1.5 N), then was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to give the title product as white solid (1.73 g, 82%).

後処理

  1. customTHF was removed
  2. washThe aqueous layer was washed with ether (100 mL)
  3. extractionwas extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-bc6595eb075e40e1b14ec163d31d4b92
出典データセット
uspto-grants-2011_08
特許番号
US08008302B2

反応ノート

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