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

HRID 1390216

Reaktionsgleichung

Reaktionsgleichung von HRID 1390216
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:14])[C:11]([OH:13])=O)=[CH:9][C:4]=2[CH2:3][CH2:2]1.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.C(OC(Cl)=O)C(C)C.[NH2:35][CH:36]1[C:42](=[O:43])[N:41]2[CH:37]1[S:38][C:39]([CH3:48])([CH3:47])[CH:40]2[C:44]([OH:46])=[O:45].C(=O)(O)[O-].[Na+]>O.C(N(CC)CC)C.O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:14])[C:11]([NH:35][CH:36]3[C:42](=[O:43])[N:41]4[CH:37]3[S:38][C:39]([CH3:48])([CH3:47])[CH:40]4[C:44]([OH:46])=[O:45])=[O:13])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Komponenten

9

Edukt 5

HCID 1626-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 11708267BistrimethylsilylacetamidHCID 233358212-(2,3-Dihydrobenzofuran-5-yl)-2-hydroxyacetic acid

Produkt 1

HCID 227484976-[[(2,3-Dihydro-5-benzofuranyl)hydroxyacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×HCID 8471TriethylamineLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

(2,3-Dihydro-5-benzofuranyl)hydroxyacetic acid (10 mmole), triethylamine (10 mmole) and bistrimethylsilylacetamide (BSA) (10 mmole) are added to 50 ml of tetrahydrofuran and refluxed for 2 hours. The reaction mixture is cooled to about -10° C. and 10 mmole of isobutylchloroformate is added dropwise. After 30 minutes at -10° C., 10 mmole of 6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid in 50 ml of water-20 ml of tetrahydrofuran containing 10 mmole of triethylamine is added dropwise to the previously prepared solution which is at about -10° C. After the addition is complete, the temperature is allowed to rise to room temperature from -10° C. About 50 ml of saturated sodium bicarbonate and 100 ml of water are added to the reaction mixture which is then twice extracted with ether. The aqueous phase is layered with ethyl acetate and the pH is adjusted to 1.5 by the addition of hydrochloric acid. The ethyl acetate is separated from the aqueous phase, dried over magnesium sulfate, filtered and evaporated to give the title compound.

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. customis at about -10° C
  3. additionAfter the addition
  4. customto rise to room temperature from -10° C
  5. extractionis then twice extracted with ether
  6. additionthe pH is adjusted to 1.5 by the addition of hydrochloric acid
  7. customThe ethyl acetate is separated from the aqueous phase
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b8cee7f8138744db9faf07d060a1c424
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04138397

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