The OCS uses a "mediation" server role to bring SIP into the OCS. ShoreTel does not yet support direct interconnection with the OCS for this purpose. Currently, ShoreTel supports the use of Audicodes media Gateway to interface the ShoreTel SG family to the OCS mediation server.
Mediant 1000 for Microsoft UC - AudioCodes PRI MSRP = $3857
MediaPack 11x for Microsoft UC - AudioCodes 8 port FXO/FXS MSRP = $822
Both these links to application notes. Basically you would make a choice on analog or digital implementation. In one case you would be setting up SIP trunks so that would require SIP licenses from ShoreTel. With analog, depending on how you set up FXO or FXS you might need some user licenses. If you let the OCS be the FXS then you would ring into the ShoreTel as a CO line. Accessing the OCS from the ShoreTel side would require and access code or a fake area code to enable that trunk group to be selected when you want calls to go out via OCS.
I suspect at somepoint, ShoreTel will eliminate the need for the Audiocodes media gateway, but it seems to be a requirement at this point. Remember product development is a process not an event!