Plymouth attorney Timothy Oliver pleaded not guilty Tuesday to federal wire fraud charges that he stole $500,000 from a Mexican construction company with the promise of work on a development project for the government of Libya.

Making his first court appearance Tuesday, Oliver entered the plea during a brief hearing before U.S. Magistrate Judge Jeanne Graham. Graham allowed Oliver to remain free on an unsecured $25,000 appearance bond but ordered him to surrender his passport and not travel outside Minnesota without government approval.

Oliver was indicted on six counts of wire fraud by a federal grand jury in May. A tentative trial date was set for Aug. 4 in front of Chief U.S. District Judge Michael Davis.

According to the charges, Oliver allegedly persuaded ARS Tectonica in 2009 to provide him with $500,000 to obtain a line of credit for a construction project in Libya.

Instead, the indictment states, Oliver spent all but $1,000 of the $500,000 for personal expenses.

Oliver also was rebuked last month by the Minnesota Department of Commerce in a consent order in which ­Oliver’s insurance license was revoked.

The department said Oliver was “unqualified to act as a licensed insurance producer” because of a number of legal judgments and court findings against him in several lawsuits.

In a 2011 case in federal court, U.S. District Judge Donovan Frank found that Oliver, a business associate and a number of real estate partnerships made “fraudulent misrepresentations” in providing collateral for a loan from a private firm. Frank awarded the firm, Meecorp Capital Markets, nearly $2.4 million.

Revocation of his insurance license was Oliver’s second run-in with the Commerce Department. In 2006, Oliver and a partner in a Mexican real estate project agreed to repay Minnesota investors in the Bahia Poniente project after it was determined that they sold lots without registering them with the Commerce Department under the state’s consumer protection law.