Ethanolamine → (4S)-2-(4-(methoxycarbonyl)-2-methylphenylimino)-4-isobutyl-1,3-thiazolidine

HRID 276459

Reaction equation

HRID 276459 reaction equation
OC[C@](N)(C)CCC.CO[C:11](=O)[C@H:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[NH2:13].OCCN.[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[S:35])=[C:29]([CH3:36])[CH:28]=1)=[O:26]>>[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]2[NH:13][C@@H:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:11][S:35]2)=[C:29]([CH3:36])[CH:28]=1)=[O:26]

Participants

5

Reactant 4

HCID 700EthanolamineHCID 65105(+)-L-Leucine methyl esterHCID 18316033Methyl 4-isothiocyanato-3-methylbenzoateHCID 58649528(S)-2-amino-2-methylpentan-1-ol

Product 1

HCID 178498123(4S)-2-(4-(methoxycarbonyl)-2-methylphenylimino)-4-isobutyl-1,3-thiazolidine

Procedure

(1S)-1-(Hydroxymethyl)-1-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. 4-(Methoxycarbonyl)-2-methylphenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1a to give (4S)-2-(4-(methoxycarbonyl)-2-methylphenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give (4S)-2-(4-(methoxycarbonyl)-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine. The thiazolidine was saponified according to Method D6a, Step 1 to give (4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine. The acid was coupled with ammonia as described in Method D6a, Step 2 to afford (4S)-2-(4-carbamoyl-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine.

Sources & evidence

ORD record
ord-a606d5240cfc4bbebd696b95707fa795
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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