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

HRID 1677771노트

반응식

HRID 1677771 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bc6595eb075e40e1b14ec163d31d4b92
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008302B2

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