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

HRID 1833427Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-b45fe0df559c4ba988bc9912611c273d
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04066657

Reaction notes

Loading…