1-Bromo-2-methylpropane → (4S)-2-(4-cyano-3-(trifluoromethyl)phenylimino)-4-(2-butyl)-3-isobutyl-1,3-thiazolidine
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]2[NH:14][C@@H:13]([CH:15]([CH2:17][CH3:18])[CH3:16])[CH2:12][S:11]2)=[CH:5][C:4]=1[C:19]([F:22])([F:21])[F:20])#[N:2].[CH2:23](Br)[CH:24]([CH3:26])[CH3:25]>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]2[N:14]([CH2:23][CH:24]([CH3:26])[CH3:25])[C@@H:13]([CH:15]([CH2:17][CH3:18])[CH3:16])[CH2:12][S:11]2)=[CH:5][C:4]=1[C:19]([F:22])([F:21])[F:20])#[N:2]Participants
3
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-Cyano-3-(trifluoromethyl)aniline was converted to 4-cyano-3-(trifluoromethyl)phenyl isothiocyanate according to A2a, Step 3. The isothiocyanate was reacted with (1S)-1-(chloromethyl)-2-methylbutanammonium chloride according to Method C1a to give (4S)-2-(4-cyano-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-cyano-3-(trifluoromethyl)phenylimino)-4-(2-butyl)-3-isobutyl-1,3-thiazolidine.
Sources & evidence
- ORD record
- ord-16655e1d211c41d4a38ddf5603263953
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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