Boc-L-Valine → Carbamic acid, [(1R)-1-(2-hydroxyethyl)-2-methylpropyl]-, 1,1-dimethylethyl

Participants

Reaction Steps

N-(tert-Butoxycarbonyl)-(L)-valine was converted to (S)-3-(tert-butoxycarbonylamino)-1-diazo-4-methylpentan-2-one according to Method B6a, Step 1. The diazo compound was converted to methyl (R)-3-(tert-butoxycarbonylamino)-4-methylpentanoate according to Method B6a, Step 2. The ester was reduced according to Method B6a, Step 3 to give (R)-3-(tert- butoxycarbonylamino)-4-methylpentan-1-ol. The carbamate was deprotected and converted to (R)-3-amino-1-chloro-4-methylpentane according to Method B7e. The 3-chloropropylamine was treated with 2-methyl-4-nitrophenyl isothiocyanate according to Method C2a to give (4R)-2-(2-methyl-4-nitrophenylimino)-4-isopropyl-1,3-thiazine. The thiazine was alkylated with isobutyl bromide according to Method D2a to afford (4R)-2-(2-methyl-4-nitrophenylimino)-3-isobutyl-4-isopropyl-1,3-thiazine HCl salt.

Provenance & Evidence