Pyridine → (2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

HRID 851631노트

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HRID 851631 반응식
C([N+](CCCC)(CCCC)CCCC)CCC.C1(CC([NH:27][C@H:28]2[C@H:31]([CH3:32])[N:30]([S:33]([O-:36])(=[O:35])=[O:34])[C:29]2=[O:37])=O)C=CC=CC=1.N1C=CC=CC=1.C(Cl)(Cl)=O.FC(F)(F)C(O)=O>C(Cl)Cl.C1C=CC=CC=1.CO>[NH2:27][C@H:28]1[C@H:31]([CH3:32])[N:30]([S:33]([OH:36])(=[O:34])=[O:35])[C:29]1=[O:37]

참가 물질

8

반응물 4

HCID 1049PyridineHCID 6371PhosgeneHCID 6422Trifluoroacetic acidHCID 131713000(3S-trans)-4-methyl-2-oxo-3-(phenylacetylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt

생성물 1

HCID 133361(2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid수율 34%

시약·촉매·용매 3

HCID 241Benzene용매HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
-15 °C

실험 절차

(3S-trans)-3-[(Phenylacetyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid, tetra-n-butylammonium salt (3.79 g) is dissolved in 70 ml of methylene chloride, cooled to -15° C. and 2.3 ml of pyridine is added. The cold mixture is treated with 5.8 ml of a 12% mixture of phosgene in benzene and stirred at -10° C. for 90 minutes. Methanol (35 ml) is added and the mixture is stirred for 30 minutes followed by the addition of 1.62 ml of trifluoroacetic acid. The reaction mixture is allowed to warm to room temperature and stirred for 16 hours. The precipitated material is collected by filtration, washed with methylene chloride and dried to yield 0.43 g of the title compound.

후처리

  1. stirringthe mixture is stirred for 30 minutes
  2. temperatureto warm to room temperature
  3. stirringstirred for 16 hours
  4. filtrationThe precipitated material is collected by filtration
  5. washwashed with methylene chloride
  6. customdried

출처 및 근거

ORD 기록
ord-05a6839c0e69449b9369abec182dd6e7
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04386034

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