Sodium hydride → HCID 69796701, 화합물

HRID 984429노트

반응식

HRID 984429 반응식
[CH3:1][CH:2]([C:13]([CH3:15])=[O:14])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[H-].[Na+].[Si:18]([O:25][C@@H:26]([C@@H:28]1[C@@H:31](SC2C=CC=CC=2)[NH:30][C:29]1=[O:39])[CH3:27])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[Cl-].[NH4+]>O1CCCC1>[Si:18]([O:25][C@@H:26]([C@@H:28]1[C@@H:31]([C:2]([C:13](=[O:14])[CH3:15])([C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])[CH3:1])[NH:30][C:29]1=[O:39])[CH3:27])([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 440192Benzyl 2-methyl-3-oxobutanoateHCID 11089029HCID 11089029, 화합물

생성물 1

HCID 69796701HCID 69796701, 화합물수율 77.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Benzyl 2-methylacetoacetate (825 mg, 4.00 mmole) was added to a suspension of sodium hydride (160 mg, 4.0 mmole) in tetrahydrofuran (10 ml) in a nitrogen stream, and the solution mixture was stirred for 10 min at room temperature and then admixed with cuprous bromide dimethylsulfide complex (822 mg, 5.98 mmole), followed by stirring for 1 hour, addition of (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-phenylthio-2-azetidinone (677 mg, 2.00 mmole) and stirring for 3 hours. The reaction solution was admixed with saturated ammonium chloride solution, and after the insoluble matters were removed by filtration, the filtrate was extracted with ethyl acetate. The ethyl acetate layer was washed with aqueous saturated sodium chloride solution three times, dried over magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (the developing solvent was a 3:1 mixture of n-hexane and ethyl acetate) to give 673 mg (77.6%) of the subject compound consisting of a diastereomer mixture (Products A and B) at a ratio of about 1:1 in the form of colorless oily matter.

후처리

  1. stirringby stirring for 1 hour
  2. stirringstirring for 3 hours
  3. customafter the insoluble matters were removed by filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with aqueous saturated sodium chloride solution three times
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (the developing solvent
  9. additiona 3:1 mixture of n-hexane and ethyl acetate)

출처 및 근거

ORD 기록
ord-089d43a2917a4dd2801a0ca57c36a377
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867297B1

반응 노트

불러오는 중…