Ethanolamine → N-((1S)-1-(benzylthiomethyl)-2-chloroethyl)-N-isobutylammonium chloride

HRID 276501

Reaction equation

HRID 276501 reaction equation
C(SC[C@@H](N)CO)C1C=CC=CC=1.OCCN.[CH:18]([CH:21]1[NH:25][C@H:24]([CH2:26][S:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23]O1)([CH3:20])[CH3:19].O1CCNC1.C(SC[C@@H](NCC(C)C)CO)C1C=CC=CC=1.O=S(Cl)[Cl:59]>>[Cl-:59].[CH2:28]([S:27][CH2:26][C@H:24]([NH2+:25][CH2:21][CH:18]([CH3:20])[CH3:19])[CH2:23][Cl:59])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 6

HCID 700Ethanolamine2×HCID 24386Thionyl ChlorideHCID 5366831,3-OxazolidineHCID 2817366(1S)-1-(Benzylthiomethyl)-2-hydroxyethylamineHCID 57283350(4S)-2-isopropyl-4-(benzylthiomethyl)-1,3-oxazolidineHCID 69992249N-((1S)-1-(benzylthiomethyl)-2-hydroxyethyl)-N-isobutylamine

Product 1

HCID 69993869N-((1S)-1-(benzylthiomethyl)-2-chloroethyl)-N-isobutylammonium chloride

Procedure

(1S)-1-(Benzylthiomethyl)-2-hydroxyethylamine was made from (L)-S-benzylcysteine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (4S)-2-isopropyl-4-(benzylthiomethyl)-1,3-oxazolidine according to Method B4c, Step 1. The oxazolidine was reduced to N-((1S)-1-(benzylthiomethyl)-2-hydroxyethyl)-N-isobutylamine according to Method B4c, Step 2. The resulting 2-hydroxyethylamine was treated with SOCl2 according to Method B7c to give N-((1S)-1-(benzylthiomethyl)-2-chloroethyl)-N-isobutylammonium chloride. 2-Ethyl-4-cyanophenyl isothiocyanate was reacted with N-((1S)-1-(benzylthiomethyl)-2-chloroethyl)-N-isobutylammonium chloride according to Method C1b to give (4S)-2-(2-ethyl-4-cyanophenylimino)-4-(benzylthiomethyl)-3-isobutyl-1,3-thiazolidine HCl salt.

Sources & evidence

ORD record
ord-79208f749d0e4332944ea4e565a6e6f7
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

Loading…