7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid → 7-[[(1H-Indol-1-yl)acetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 2050379

Reaktionsgleichung

Reaktionsgleichung von HRID 2050379
[N:1]1([CH2:10][C:11]([OH:13])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(OC(Cl)=O)C(C)C.[NH2:22][CH:23]1[C:30](=[O:31])[N:29]2[CH:24]1[S:25][CH2:26][C:27]([Cl:35])=[C:28]2[C:32]([OH:34])=[O:33].O1CCCC1.O>O1CCCC1.C(N(CC)CC)C>[N:1]1([CH2:10][C:11]([NH:22][CH:23]2[C:30](=[O:31])[N:29]3[CH:24]2[S:25][CH2:26][C:27]([Cl:35])=[C:28]3[C:32]([OH:34])=[O:33])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

7

Edukt 4

HCID 409577-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 62365Isobutyl chloroformateHCID 904481H-Indole-1-acetic acidHCID 21881883Oxolane--water (1/1)

Produkt 1

HCID 233358177-[[(1H-Indol-1-yl)acetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

(1H-Indol-1-yl)acetic acid (0.05 m) is added to tetrahydrofuran. The temperature is lowered to about -10° C. and 1 equivalent of isobutylchloroformate in tetrahydrofuran is added. This mixture is stirred for about 30 minutes. A solution of 7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid in 1:1 tetrahydrofuran/water containing 1 equivalent of triethylamine is added to the previously formed solution maintained at -10° C. The resulting solution is stirred for about 60 minutes at -10° C. to 0° C. and then stirred for 60 minutes at 30° C. to 30° C. The solvents are removed at reduced pressure to give a residue which is extracted with ethyl acetate. The ethyl acetate is dried over magnesium sulfate, filtered and evaporated to give the title compound.

Aufarbeitung

  1. customis lowered to about -10° C.
  2. stirringThe resulting solution is stirred for about 60 minutes at -10° C. to 0° C.
  3. stirringstirred for 60 minutes at 30° C. to 30° C
  4. customThe solvents are removed at reduced pressure
  5. customto give a residue which
  6. extractionis extracted with ethyl acetate
  7. dry with materialThe ethyl acetate is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-824b117ad170400cb42ee3da208f28d2
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04200747

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