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

HRID 851631ノート

反応式

HRID 851631 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-15 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-05a6839c0e69449b9369abec182dd6e7
出典データセット
uspto-grants-1983_05
特許番号
US04386034

反応ノート

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