6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid → 6-[[Carboxy(2,3-dihydro-5-benzofuranyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

HRID 1390217

Reaktionsgleichung

Reaktionsgleichung von HRID 1390217
[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.[NH2:21][CH:22]1[C:28](=[O:29])[N:27]2[CH:23]1[S:24][C:25]([CH3:34])([CH3:33])[CH:26]2[C:30]([OH:32])=[O:31].C(N(CC)CC)C.Cl>CN(C)C=O.C(OCC)(=O)C.CCOCC.O>[C:5]([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:1]([NH:21][CH:22]1[C:28](=[O:29])[N:27]2[CH:23]1[S:24][C:25]([CH3:34])([CH3:33])[CH:26]2[C:30]([OH:32])=[O:31])=[O:3])([OH:7])=[O:6]

Komponenten

10

Edukt 5

HCID 1626-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 23335822alpha-Carboxy(2,3-dihydro-5-benzofuranyl)acetic acid

Produkt 1

HCID 227485116-[[Carboxy(2,3-dihydro-5-benzofuranyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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 6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (14 mmole), 30 ml of water, 15 ml of ether and triethylamine (14 mmole). After stirring for 30 minutes the pH is adjusted to 1.5 with dilute hydrochloric acid and the layers separated. The ether layer 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.

Aufarbeitung

  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 layer is extracted with water
  6. customEvaporation of the ether
  7. customgives a residue which
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6ccf7b79b97c4ee3bf70516142535ddb
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04138397

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