Boc-L-Valine → Carbamic acid, [(1R)-1-(2-hydroxyethyl)-2-methylpropyl]-, 1,1-dimethylethyl
Reaction equation
C(OC(N[C@H](C(O)=O)C(C)C)=O)(C)(C)C.C(OC(N[C@@H](C(C)C)C(=O)C=[N+]=[N-])=O)(C)(C)C.[C:33]([O:37][C:38]([NH:40][C@@H:41]([CH:47]([CH3:49])[CH3:48])[CH2:42][C:43](OC)=[O:44])=[O:39])([CH3:36])([CH3:35])[CH3:34]>>[C:33]([O:37][C:38]([NH:40][C@@H:41]([CH:47]([CH3:49])[CH3:48])[CH2:42][CH2:43][OH:44])=[O:39])([CH3:36])([CH3:35])[CH3:34]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-f910507575bb4c2fa9cf5b58b110a0cf
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
Loading…