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

HRID 904024Notes

Reaction equation

HRID 904024 reaction equation
[C:1]([CH:4]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH2:14][CH2:13][C:12]=2[CH:16]=1)[C:5]([OH:7])=[O:6])([OH:3])=O.S(Cl)(Cl)=O.[C:21]([O:24][CH2:25][C:26]1[CH2:33][S:32][CH:31]2[N:28]([C:29](=[O:35])[CH:30]2[NH2:34])[C:27]=1[C:36]([OH:38])=[O:37])(=[O:23])[CH3:22].C(N(CC)CC)C.Cl>CN(C)C=O.C(OCC)(=O)C.CCOCC.O>[C:21]([O:24][CH2:25][C:26]1[CH2:33][S:32][CH:31]2[N:28]([C:29](=[O:35])[CH:30]2[NH:34][C:1](=[O:3])[CH:4]([C:5]([OH:7])=[O:6])[C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH2:14][CH2:13][C:12]=3[CH:16]=2)[C:27]=1[C:36]([OH:38])=[O:37])(=[O:23])[CH3:22]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 24386Thionyl ChlorideHCID 23335822alpha-Carboxy(2,3-dihydro-5-benzofuranyl)acetic acid

Product 1

HCID 233358323-[(Acetyloxy)methyl]-7-[[carboxy(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 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

α-Carboxy-(2,3-dihydro-5-benzofuranyl)acetic acid (14 mmole) is added to 50 ml of ether. Thionyl chloride (14.5 mmole) is added along with 1 drop of dimethylformamide. This mixture is refluxed about 3 hours and then evaporated under reduced pressure at room temperature. The residue is added to 50 ml of ether which is added to an ice-cold mixture of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (14 mmole), 30 ml of water 15 ml of ether, 14 mmole of triethylamine. After 30 minutes the pH is adjusted to 1.5 with dilute hydrochloric acid and the layers separated. The ether is extracted with water. Evaporation of the ether gives a residue which is taken up in ethyl acetate, dried, filtered and evaporated to give the title compound.

Workup

  1. temperatureThis mixture is refluxed about 3 hours
  2. customevaporated under reduced pressure at room temperature
  3. additionThe residue is added to 50 ml of ether which
  4. customthe layers separated
  5. extractionThe ether is extracted with water
  6. customEvaporation of the ether
  7. customgives a residue which
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-1260c8cbe97f409aa00d42d88700f166
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

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