Ethyl iodoacetate → Ethyl (3-benzyloxycarbonylamino-6-methyl-2-oxo-1,2-dihydro-1-pyridyl)acetate

HRID 2257100노트

반응식

HRID 2257100 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:19])[NH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O.Cl>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][N:14]1[C:15]([CH3:18])=[CH:16][CH:17]=[C:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C:13]1=[O:19])[CH3:28]

참가 물질

6

반응물 3

HCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 100838403-Benzyloxycarbonylamino-6-methyl-2-pyridone

생성물 1

HCID 18323889Ethyl (3-benzyloxycarbonylamino-6-methyl-2-oxo-1,2-dihydro-1-pyridyl)acetate수율 55.5%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매

실험 절차

The compound of Example 13 (1.80 g, 7.0 mmole) was added to a stirred suspension of sodium hydride (0.33 g, 8.4 mmole) in dry dimethylformamide (50 mL). After 45 minutes, ethyl iodoacetate (1.43 g, 6.7 mmole) was added, and the mixture was stirred overnight, diluted with 10% hydrochloric acid (300 mL) and extracted with ethyl acetate (3×150 mL). The organic layer was washed with brine (twice), dried and evaporated. The resulting yellow, wary solid was chromatographed, eluting with 3% ethyl acetate in dichloromethane, to give the title compound (1.28 g, 53% yield). Rf =0.52 (silica gel, 5:95 methanol:dichloromethane). Fast atom bombardment mass spectrometry confirmed the theoretical molecular weight of 344.

후처리

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe organic layer was washed with brine (twice),
  3. customdried
  4. customevaporated
  5. customThe resulting yellow, wary solid was chromatographed
  6. washeluting with 3% ethyl acetate in dichloromethane

출처 및 근거

ORD 기록
ord-d1f2a6517ce64604936485f1c05e87ef
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05656645

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