Triethylamine → 3-[(Acetyloxy)methyl]-7-[[(2,3-dihydro-5-benzofuranyl)-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 904023Notes

Reaction equation

HRID 904023 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([OH:13])=O)=[CH:9][C:4]=2[CH2:3][CH2:2]1.C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[C:29]([O:32][CH2:33][C:34]1[CH2:41][S:40][CH:39]2[N:36]([C:37](=[O:43])[CH:38]2[NH2:42])[C:35]=1[C:44]([OH:46])=[O:45])(=[O:31])[CH3:30]>C1COCC1>[C:29]([O:32][CH2:33][C:34]1[CH2:41][S:40][CH:39]2[N:36]([C:37](=[O:43])[CH:38]2[NH:42][C:11](=[O:13])[CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)[C:35]=1[C:44]([OH:46])=[O:45])(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 62365Isobutyl chloroformateHCID 27374552,3-Dihydro-5-benzofuranacetic acid

Product 1

HCID 233358433-[(Acetyloxy)methyl]-7-[[(2,3-dihydro-5-benzofuranyl)-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 10 mmole of 2,3-dihydo-5-benzofuranyl acetic acid and 10 mmole of triethylamine in 100 ml of THF is cooled to about 0° C. While stirring, isobutylchloroformate (10 mmole) is added and the temperature maintained at 0° C. for 15 minutes. A cold solution of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (10 mmole) and 10 mmole of triethylamine in 80 ml of 50% aqueous THF is added to the previously prepared solution. The mixture is stirred at 5° C. for 1 hour and at room temperature for 1 hour. Then the THF is evaporated and the residue is dissolved in water and washed with ethyl acetate. The aqueous phase is covered with ethyl acetate and the pH is adjusted to 3 with 6N hydrochloric acid. The mixture is filtered and the layers separated. The ethyl acetate is dried over magnesium sulfate, filtered and evaporated to give the title compound.

Workup

  1. stirringThe mixture is stirred at 5° C. for 1 hour and at room temperature for 1 hour
  2. customThen the THF is evaporated
  3. dissolutionthe residue is dissolved in water
  4. washwashed with ethyl acetate
  5. filtrationThe mixture is filtered
  6. customthe layers separated
  7. dry with materialThe ethyl acetate is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-82f1f8ab67ed48a39acb72412b348372
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

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