Ethanolamine → HCID 178426460, compound

HRID 276454Notes

Reaction equation

O[CH2:2][C@@H:3]([NH2:8])[CH2:4][CH:5]([CH3:7])[CH3:6].COC(=O)[C@H](CC(C)C)N.OCCN.[Cl:23][C:24]1[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[C:26]([CH3:32])[C:25]=1[N:33]=[C:34]=[S:35]>>[Cl:23][C:24]1[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[C:26]([CH3:32])[C:25]=1[N:33]=[C:34]1[NH:8][C@@H:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[CH2:2][S:35]1

Participants

Reactant 4

HCID 700Ethanolamine

HCID 65105(+)-L-Leucine methyl ester

HCID 111307L-Leucinol

HCID 18316278HCID 18316278, compound

Product 1

HCID 178426460HCID 178426460, compound

Procedure

(1S)-1-(Hydroxymethyl)-3-methylbutylamine was made from (L)-leucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (1S) -1-(chloromethyl)-3-methylbutanammonium chloride as described in Method B7a. 2-Chloro-4-cyano-6-methylphenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1c to give (4S)-2-(2-chloro4-cyano-6-methylphenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2f to afford (4S)-2-(2-chloro-4-cyano-6-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine trifluoroacetate salt.

Sources & evidence

ORD record: ord-c78b179939f44bd394fca26ad903493f
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

Loading…