YOU SAID:

I was tired until I woke up from my nap.

INTO JAPANESE

昼寝から覚めたまで疲れていました

BACK INTO ENGLISH

Until I was tired, waking up from a NAP

INTO JAPANESE

私は疲れて、昼寝から目を覚ますまで

BACK INTO ENGLISH

I am tired, waking up from a NAP to

INTO JAPANESE

私は疲れて、昼寝から目を覚ます

BACK INTO ENGLISH

I am tired, waking up from a NAP

INTO JAPANESE

私は疲れて、昼寝から目を覚ます

BACK INTO ENGLISH

I am tired, waking up from a NAP