Ethanolamine → (4S)-2-(4-cyano-2,5-dimethylphenylimino)-4-(2-butyl)-1,3-thiazolidine

HRID 276488Notes

Reaction equation

HRID 276488 reaction equation
OC[C@@H](N)C(C)CC.COC(=O)[C@H]([C@H](CC)C)N.OCCN.[CH3:23][C:24]1[CH:31]=[C:30]([N+:32]([O-])=O)[C:29]([CH3:35])=[CH:28][C:25]=1[C:26]#[N:27].NC1C=CC=CC=1.C([C:45]1C(C)=[CH:49][C:48]([N:52]=[C:53]=[S:54])=[C:47]([CH3:55])[CH:46]=1)#N>>[C:26]([C:25]1[C:24]([CH3:23])=[CH:31][C:30]([N:32]=[C:53]2[NH:52][C@@H:48]([CH:47]([CH2:46][CH3:45])[CH3:55])[CH2:49][S:54]2)=[C:29]([CH3:35])[CH:28]=1)#[N:27]

Participants

7

Reactant 6

HCID 700EthanolamineHCID 6115AnilineHCID 52273Benzonitrile, 2,5-dimethyl-4-nitro-HCID 75735L-Isoleucine, methyl esterHCID 11789185(2S)-2-amino-3-methylpentan-1-olHCID 183161804-Cyano-2,5-dimethylphenyl isothiocyanate2×

Product 1

HCID 178445840(4S)-2-(4-cyano-2,5-dimethylphenylimino)-4-(2-butyl)-1,3-thiazolidine

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. 2,5-Dimethyl-4-nitrobenzonitrile was converted to 4-cyano-2,5-methylaniline according to Method A1a. The aniline was converted to 4-cyano-2,5-dimethylphenyl isothiocyanate as described in Method A2a, Step 3. 4-Cyano-2,5-dimethylphenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-2-methylbutanammonium chloride to Method C1a to give (4S)-2-(4-cyano-2,5-dimethylphenylimino)-4-(2-butyl)-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give (4S)-2-(4-cyano-2,5-dimethylphenylimino)-4-butyl-3-isobutyl-1,3-thiazolidine.

Sources & evidence

ORD record
ord-878ab8ef8f7a46ecb8170d7eef8f62d9
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

Loading…