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

HRID 1762167노트

반응식

HRID 1762167 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9d1d13677cfb427a82806909097c676f
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04831026

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