Microsoft has said that its offer to buy the US operations of hugely popular video-sharing app TikTok has been rejected, paving the way for Oracle to secure a last-minute deal.
US President Donald Trump gave a 15 September deadline for the Chinese-owned app to sell or shut down.
The Trump administration claims TikTok and other Chinese apps are national security threats.
Microsoft and Oracle led the race to buy TikTok from Chinese firm ByteDance.
Microsoft announced that “ByteDance let us know today they would not be selling TikTok’s US operations to Microsoft. We are confident our proposal would have been good for TikTok’s users, while protecting national security interests.”
“We look forward to seeing how the service evolves in these important areas,” its statement added.
This paves the way for Oracle, who Mr Trump said would be “a great company” to take over TikTok’s US operations last month.
Oracle’s chairman Larry Ellison is a supporter of Mr Trump and held a fundraising event for him in February.
TikTok is a hugely popular video-sharing app – which has been downloaded two billion times globally – where people make and upload 15-second clips.
The Wall Street Journal and Reuters reported that Oracle, which sells database technology and cloud systems to businesses, had won the bidding war, citing people familiar with the matter.
Earlier reports said Oracle was seriously considering buying TikTok’s businesses in the US, Canada, Australia and New Zealand with investment firms, including General Atlantic and Sequoia Capital.
Mr Trump ordered TikTok’s owner ByteDance to sell its US business within 90 days or face being shut down.The forced sale of TikTok’s US business is part of a wider crackdown on Chinese technology firms in America.
Mr Trump has said apps such as TikTok, WeChat and equipment maker Huawei pose a national security threat because data collected about users can be shared with the Chinese government. The Chinese firms deny this claim.