6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid → 6-[[Amino[4-hydroxy-3-(methoxymethyl)phenyl]acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

HRID 2049224ノート

反応式

HRID 2049224 の反応式
C(OC(=O)C=C([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH2:20]N=[N+]=[N-])[CH:14]=1)[C:10]([OH:12])=O)C)C.[CH2:25]([O:27]C(Cl)=O)C.[NH2:31][CH:32]1[C:38](=[O:39])[N:37]2[CH:33]1[S:34][C:35]([CH3:44])([CH3:43])[CH:36]2[C:40]([OH:42])=[O:41].O1CCCC1.O>C(N(CC)CC)C.O1CCCC1>[NH2:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH2:20][O:27][CH3:25])[CH:14]=1)[C:10]([NH:31][CH:32]1[C:38](=[O:39])[N:37]2[CH:33]1[S:34][C:35]([CH3:44])([CH3:43])[CH:36]2[C:40]([OH:42])=[O:41])=[O:12]

参加物

7

反応物 4

HCID 1626-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidHCID 10928Ethyl chloroformateHCID 21881883Oxolane--water (1/1)HCID 86736918alpha-(3-Ethoxy-1-methyl-3-oxo-1-propen-1-yl)amino-3-(azidomethyl)-4-hydroxybenzeneacetic acid

生成物 1

HCID 203447696-[[Amino[4-hydroxy-3-(methoxymethyl)phenyl]acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

反応条件

温度
-10 °C

実験手順

α-(3-Ethoxy-1-methyl-3-oxo-1-propen-1-yl)amino-3-(azidomethyl)-4-hydroxybenzeneacetic acid (0.05 mole) is added to tetrahydrofuran (THF) at -10° C. Ethylchloroformate (0.05 mole) is slowly added with stirring while maintaining the temperature at -10° C. After 30 minutes, 6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylic acid in 1 to 1 mixture of THF/water containing 0.05 mole of triethylamine is added to the thus formed solution. The mixture is stirred at -10° C. for about 30 minutes and then at about 20° C. for 30 minutes. The pH is adjusted to 2 and the reaction mixture is extracted with ethyl ether. The pH is then adjusted to 4.5 to 5.5 and the reaction mixture is extracted with ethyl acetate. The ethyl acetate is dried over sodium sulfate, filtered to remove the drying agent and evaporated to give the title compound.

後処理

  1. additionis added to the thus formed solution
  2. stirringThe mixture is stirred at -10° C. for about 30 minutes
  3. waitat about 20° C. for 30 minutes
  4. extractionthe reaction mixture is extracted with ethyl ether
  5. extractionthe reaction mixture is extracted with ethyl acetate
  6. dry with materialThe ethyl acetate is dried over sodium sulfate
  7. filtrationfiltered
  8. customto remove the drying agent
  9. customevaporated

出典と根拠

ORDレコード
ord-d8a925f27058449d823952ac495146c3
出典データセット
uspto-grants-1980_04
特許番号
US04197240

反応ノート

読み込み中…