1-Bromo-2-methylpropane → (4S)-2-(4-chloro-3-(trifluoromethyl)phenylimino)-4-(2-butyl)-3-isobutyl-1,3-thiazolidine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[NH:13][C@@H:12]([CH:14]([CH2:16][CH3:17])[CH3:15])[CH2:11][S:10]2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[CH2:22](Br)[CH:23]([CH3:25])[CH3:24]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[N:13]([CH2:22][CH:23]([CH3:25])[CH3:24])[C@@H:12]([CH:14]([CH2:16][CH3:17])[CH3:15])[CH2:11][S:10]2)=[CH:4][C:3]=1[C:18]([F:19])([F:21])[F:20]Participants
Procedure
(1S)-1-(Hydroxymethyl)-2-methylbutylamine was made from (L)-isoleucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (1S)-1-(chloromethyl)-2-methylbutanammonium chloride as described in Method B7a. 4-Chloro-3-(trifluoromethyl)aniline was converted to 4-chloro-3-(trifluoromethyl)phenyl isothiocyanate according to Method A2a, Step 3 4-Chloro-3-(trifluoromethyl)phenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-2-methylbutanammonium chloride according to Method C1a to give (4S)-2-(4-chloro-3-(trifluoromethyl)phenylimino)-4-(2-butyl)-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford (4S)-2-(4-chloro-3-(trifluoromethyl)phenylimino)-4-(2-butyl)-3-isobutyl-1,3-thiazolidine.
Sources & evidence
- ORD record
- ord-0de3f4bea96f42838ff0db403371108d
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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