Propylene Oxide → (3R,4R)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-4-methylsulfonyl-2-oxoazetidine

HRID 653247노트

반응식

HRID 653247 반응식
O=C(Cl)OC(Cl)(Cl)Cl.[Cl:9][CH2:10][C:11]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19](=[N:23][O:24][CH3:25])[C:20]([OH:22])=O)[N:18]=1)=[O:12].[NH2:26][C@H:27]1[C@@H:30]([S:31]([CH3:34])(=[O:33])=[O:32])[NH:29][C:28]1=[O:35].C1OC1C>C(Cl)Cl.CC(N(C)C)=O.C(N(CC)CC)C.CN(C=O)C>[Cl:9][CH2:10][C:11]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19](=[N:23][O:24][CH3:25])[C:20]([NH:26][C@H:27]2[C@@H:30]([S:31]([CH3:34])(=[O:33])=[O:32])[NH:29][C:28]2=[O:35])=[O:22])[N:18]=1)=[O:12]

참가 물질

9

반응물 4

HCID 6378Propylene OxideHCID 10426DiphosgeneHCID 581157C8H8ClN3O4SHCID 53637648(3R,4R)-3-amino-4-methylsulfonyl-2-oxoazetidine

생성물 1

HCID 53860321(3R,4R)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-4-methylsulfonyl-2-oxoazetidine수율 70.2%

시약·촉매·용매 4

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매2회HCID 31374Dimethylacetamide용매

실험 절차

To a solution of 0.122 g of DMF in 5 ml of methylene chloride is added 0.10 ml of diphosgene at -10° C. The mixture is stirred for 30 minutes at room temperature, then cooled to a temperature of -70° C., followed by dropwise addition of 10 ml of methylene chloride solution containing 0.427 g of 2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetic acid and 0.17 g of triethylamine. The mixture is stirred for 2 hours at a temperature ranging from -25° to -20° C., which is cooled to a temperature of -70° C., to which are added 0.17 g of triethylamine, a solution of 0.229 g of (3R,4R)-3-amino-4-methylsulfonyl-2-oxoazetidine in 3 ml of DMA, and 2 ml of propylene oxide, successively. The temperature of the mixture is raised up to room temperature in the course of 1.5 hours. The reaction mixture is concentrated under reduced pressure, and the residue is purified on a silica-gel column (ethyl acetate:n-hexane=1:1) to give 0.415 g of (3R,4R)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-4-methylsulfonyl-2-oxoazetidine. This is in agreement with the compound (syn-isomer) obtained in Reference Example 15B in IR and NMR.

후처리

  1. temperaturecooled to a temperature of -70° C.
  2. stirringThe mixture is stirred for 2 hours at a temperature
  3. customranging from -25° to -20° C.
  4. temperaturewhich is cooled to a temperature of -70° C., to which
  5. temperatureThe temperature of the mixture is raised up to room temperature in the course of 1.5 hours
  6. concentrationThe reaction mixture is concentrated under reduced pressure
  7. customthe residue is purified on a silica-gel column (ethyl acetate:n-hexane=1:1)

출처 및 근거

ORD 기록
ord-c5f248dea0954d998a5f270ab1bf1ec4
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04675397

반응 노트

불러오는 중…