Perl 5 -p, 5755 bytes
s/\d+\D+\d+ (?=(\d+))/(1ドル-$&).$"/ge;s/\d+$//;s/^(.+?)1円*$/1ドル/
Numbers are input as a space separated list. Output is the same format.
Perl 5 -p, 55 bytes
s/\d+ (?=(\d+))/(1ドル-$&).$"/ge;s/\d+$//;s/^(.+?)1円*$/1ドル/
Numbers are input as a space separated list. Output is the same format.