YOU SAID:
He eyed them angrily as he passed.
INTO JAPANESE
彼は怒って、彼が通り過ぎると目を覚ました。
BACK INTO ENGLISH
He got angry and awoke when he passed by.
INTO JAPANESE
彼は怒って、彼が通り過ぎたときに目を覚ました。
BACK INTO ENGLISH
He got angry and awoke when he passed by.
That didn't even make that much sense in English.