6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid → 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

HRID 2049227Notes

Reaction equation

HRID 2049227 reaction equation
C(OC(NC(C1C=CC(O)=C(COC)C=1)C(O)=O)=O)C1C=CC=CC=1.C(OC(Cl)=O)C(C)C.N[CH:35]1[C:41](=[O:42])[N:40]2[CH:36]1[S:37][C:38]([CH3:47])([CH3:46])[CH:39]2[C:43]([OH:45])=[O:44].C(N(CC)CC)C>O1CCCC1.O1CCCC1.O>[CH3:46][C:38]1([CH3:47])[S:37][CH:36]2[N:40]([C:41](=[O:42])[CH2:35]2)[CH:39]1[C:43]([OH:45])=[O:44]

Participants

7

Reactant 4

HCID 1626-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 20344766alpha-(Benzyloxycarbonyl)amino-4-hydroxy-3-(methoxymethyl)-benzeneacetic acid

Product 1

HCID 123140473,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
-10 °C

Procedure

α-(Benzyloxycarbonyl)amino-4-hydroxy-3-(methoxymethyl)benzeneacetic acid (0.1 mole) is dissolved in tetrahydrofuran (THF). The temperature of the solution is maintained at about -10° C. and 0.2 mole of isobutylchloroformate is added. After stirring for about 30 minutes at -10° C., 0.1 mole of 6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid in a 50/50 THF/water solution containing 0.1 mole of triethylamine is added to the above formed solution. This mixture is stirred for 30 minutes at -10° C. and then the temperature is raised to about 20° C. Stirring is continued for an additional 30 minutes. The pH is adjusted to 4.5 to 5.5, and the coupled product is extracted into ethyl acetate. The ethyl acetate is dried over magnesium sulfate, filtered and evaporated to give the coupled product, 6-[[(benzyloxycarbonyl)amino]-hydroxy-3-(methoxymethyl)-phenyl]acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.

Workup

  1. additionis added to the above formed solution
  2. stirringThis mixture is stirred for 30 minutes at -10° C.
  3. temperaturethe temperature is raised to about 20° C
  4. stirringStirring
  5. waitis continued for an additional 30 minutes
  6. extractionthe coupled product is extracted into ethyl acetate
  7. dry with materialThe ethyl acetate is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-ccc3ebfb6a584f5f9e0f4ace1eb2b64f
Source dataset
uspto-grants-1980_04
Patent number
US04197240

Reaction notes

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