How to say i waited up for him until ten o'clock. in Japanese

1)私(watashi) (pn,adj-no) i/meは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,10no dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb時(toki) (n) time/hour/moment/occasion/case/chance/opportunity/season/the times/the age/the day/tenseまでまで(made) (prt) until/till/to/up to/to/as far as/to/up to/so far as/even/only/merely寝(ne) (ok) sleepな(na) (prt) connects adj to noun/indicates emotion or emphasis/command/prohibitionい(i) (prt) strengthens a question, assertion, etc.で(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.待った待った(matta) (n) false start of a bout/backsies。(。) Japanese period "."    
watashi ha kare wo 10 toki made nena ide matta 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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2)私(watashi) (pn,adj-no) i/meは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh10no dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb時(toki) (n) time/hour/moment/occasion/case/chance/opportunity/season/the times/the age/the day/tenseまでまで(made) (prt) until/till/to/up to/to/as far as/to/up to/so far as/even/only/merely、(、) Japanese comma寝ずno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,待ってno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbいたいた(ita) (int) ouch/ow。(。) Japanese period "."    
watashi ha 10 toki made 、 nezu ni kare wo matte ita 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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company attorneys are working around the clock to complete the merger.

my superior excused me for arriving late.

i have a feeling that something is lacking in my life.

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