Ethanolamine → (4S)-2-(4-cyanophenylimino)-3,4-diisobutyl-1,3-thiazolidine

HRID 276473

Reaction equation

OC[C@@H](N)CC(C)C.COC(=O)[C@H](CC(C)C)N.OCCN.[CH3:23][CH:24]([CH3:34])[CH2:25][C@H:26]([NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:27]O.[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])[C@@H:26]([CH2:25][CH:24]([CH3:34])[CH3:23])[CH2:27][S:51]2)=[CH:47][CH:48]=1)#[N:42]

Participants

Reactant 6

HCID 700Ethanolamine2×

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 59113105(4S)-2-(4-cyanophenylimino)-3,4-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)pentan-1-ol as described in Method B4c. The resulting 2-hydroxyethylamine was converted to N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride according to Method B7c. 4-Cyanophenyl isothiocyanate was reacted with N-(1S)-1-(chloromethyl)-3methylbutyl)N-(isobutyl)ammonium chloride to Method C1f to afford (4S)-2-(4-cyanophenylimino)-3,4-diisobutyl-1,3-thiazolidine.

Sources & evidence

ORD record: ord-32ca457788204c2ab29892b4b74f8519
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Linked notes

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