Hydrogen Peroxide → HCID 22915511, 화합물

HRID 1377928노트

반응식

HRID 1377928 반응식
[C:1]([O:5][C:6]([CH2:8][CH:9]([CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=2)=[CH:30][CH:29]=1)C(N1[C@@H](CC2C=CC=CC=2)COC1=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:42]O.[Li+].[OH-].C1[CH2:50][O:49]CC1>>[C:1]([O:5][C:6]([CH2:8][CH:9]([CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=2)=[CH:32][CH:33]=1)[C:50]([OH:49])=[O:42])=[O:7])([CH3:3])([CH3:4])[CH3:2]

참가 물질

5

반응물 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 22876690HCID 22876690, 화합물

생성물 1

HCID 22915511HCID 22915511, 화합물수율 52%

반응 조건

온도
0 °C

실험 절차

To a 0° C. solution in THF (200 mL) of N-[2-tert-butyloxycarbonylmethyl-4-(4-(4-cyanophenyl)phenoxy)butanoyl]-(S)-(-)-4-benzyl-2-oxazolidinone (7.05 g, 12.7 mmol) was added 30% aqueous H2O2 (3.0 mL, 50.8 mmol) and 1M aqueous LiOH (20.3 mL, 20.3 mmol) and the reaction mixture was stirred for one hour. The reaction mixture was quenched with saturated aqueous NaHSO3 and diluted with dichloromethane. The aqueous phase was made basic with aqueous 2N NaOH and extracted twice with dichloromethane. The organic extracts were discarded and the aqueous phase was cooled to 0° C. and acidified with aqueous 2N HCl. The aqueous phase was extracted with dichloromethane and THF/dichloromethane. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (dichloromethane/10% THF/1% methanol) gave 2-tert-butyloxycarbonylmethyl-4-[4-(4-cyanophenyl)phenoxy]butanoic acid (2.6 g, 52%).

후처리

  1. customThe reaction mixture was quenched with saturated aqueous NaHSO3
  2. additiondiluted with dichloromethane
  3. extractionextracted twice with dichloromethane
  4. extractionThe aqueous phase was extracted with dichloromethane and THF/dichloromethane
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4ae1e2cafa234b70a2d6f48eb77bfff1
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665777

반응 노트

불러오는 중…