Ethanolamine → 2-(4-Cyanophenylimino)-3,5-diisobutyl-1,3-thiazolidine

HRID 276433

Reaction equation

O[CH2:2][C@@H:3](N)[CH2:4][CH:5]([CH3:7])[CH3:6].COC(=O)[C@H](CC(C)C)N.OCCN.CC(C)C[C@H]([NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])CO.[Cl-].C([NH3+])C(C)C.[C:41]([C:43]1[CH:48]=[CH:47][C:46]([N:49]=[C:50]=[S:51])=[CH:45][CH:44]=1)#[N:42]>>[C:41]([C:43]1[CH:44]=[CH:45][C:46]([N:49]=[C:50]2[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:2][CH:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[S:51]2)=[CH:47][CH:48]=1)#[N:42]

Participants

Reactant 6

HCID 700Ethanolamine

HCID 17626Benzonitrile, 4-isothiocyanato-

HCID 21133Isobutylaminehydrochloride2×

HCID 65105(+)-L-Leucine methyl ester

HCID 111307L-Leucinol

HCID 22951222(2S)-4-methyl-2-(isobutylamino)pentanol

Product 1

HCID 183164882-(4-Cyanophenylimino)-3,5-diisobutyl-1,3-thiazolidine

Procedure

(1S)-1-(Hydroxymethyl)-3-methylbutylamine was made from (L)-leucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (2S)-4-methyl-2-(isobutylamino)pentanol as described in Method B4c, Steps 1-2. The alcohol was converted to N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride as described in Method B7c. 4-Cyanophenyl isothiocyanate was reacted with N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride according to Method C1f to give 2-(4-cyanophenylimino)-3,5-diisobutyl-1,3-thiazolidine.

Sources & evidence

ORD record: ord-8aeb51ed21804895aa5affef596a2aa0
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Linked notes

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