Sodium hydride → HCID 69796701、化合物

HRID 984429ノート

反応式

HRID 984429 の反応式
[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]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 440192Benzyl 2-methyl-3-oxobutanoateHCID 11089029HCID 11089029、化合物

生成物 1

HCID 69796701HCID 69796701、化合物収率 77.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-089d43a2917a4dd2801a0ca57c36a377
出典データセット
uspto-grants-2005_03
特許番号
US06867297B1

反応ノート

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