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 2049224노트

반응식

HRID 2049224 반응식
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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

반응 조건

온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d8a925f27058449d823952ac495146c3
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04197240

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