Phenylacetyl chloride → 6-(2-Phenylacetamido)-2,2-dimethyl-3-(O-methylphosphono)penam

HRID 1833427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1833427
[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([P:10]([OH:14])([O:12][CH3:13])=[O:11])[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12.[OH-].[Na+].[C:19]1([CH2:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[C:19]1([CH2:25][C:26]([NH:1][CH:2]2[C:15](=[O:16])[N:4]3[CH:5]([P:10]([OH:14])([O:12][CH3:13])=[O:11])[C:6]([CH3:8])([CH3:9])[S:7][C@H:3]23)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 7679Phenylacetyl chlorideHCID 14798Sodium Hydroxide2×HCID 867348606-amino-2,2-dimethyl-3-(O-methylphosphono)penam

Produkt 1

HCID 867353286-(2-Phenylacetamido)-2,2-dimethyl-3-(O-methylphosphono)penam

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A stirred slurry of 532 mg. (0.002 mole) of 6-amino-2,2-dimethyl-3-(O-methylphosphono)penam in 10 ml. of water is cooled to 0° C., and the pH is then adjusted to 8.0 using 1N sodium hydroxide. To this solution is then added 0.27 ml. (310 mg., 0.002 mole) of phenylacetyl chloride, in portions, with the pH of the solution being maintained between 7 and 8 during the addition, using 0.1 N sodium hydroxide. The solution is stirred in additional 30 minutes at 0° C. and pH 7. It is concentrated in vacuo to a small volume and the title compound purified by Sephadex LH-20 chromatography, eluting with water.

Aufarbeitung

  1. additionTo this solution is then added 0.27 ml
  2. concentrationIt is concentrated in vacuo to a small volume
  3. customthe title compound purified by Sephadex LH-20 chromatography
  4. washeluting with water

Quellen und Nachweise

ORD-Eintrag
ord-b45fe0df559c4ba988bc9912611c273d
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04066657

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