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 2049224Notes

Reaction equation

HRID 2049224 reaction equation
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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-10 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d8a925f27058449d823952ac495146c3
Source dataset
uspto-grants-1980_04
Patent number
US04197240

Reaction notes

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