Ethanolamine → HCID 178445845, compound

HRID 276489

Reaction equation

HRID 276489 reaction equation
O[CH2:2][C@@H:3]([NH2:8])[CH:4]([CH3:7])[CH2:5][CH3:6].COC(=O)[C@H]([C@H](CC)C)N.OCCN.[CH3:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[C:27]([CH3:33])=[CH:26][C:25]=1[N:34]=[C:35]=[S:36]>>[CH3:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[C:27]([CH3:33])=[CH:26][C:25]=1[N:34]=[C:35]1[NH:8][C@@H:3]([CH:4]([CH2:5][CH3:6])[CH3:7])[CH2:2][S:36]1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 75735L-Isoleucine, methyl esterHCID 11789185(2S)-2-amino-3-methylpentan-1-olHCID 183163082,5-Dimethyl-4-nitrophenyl isothiocyanate2×

Product 1

HCID 178445845HCID 178445845, compound

Procedure

(1S)-1-(Hydroxymethyl)-2-methylbutylamine was made from (L)-isoleucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (1S)-1-(chloromethyl)-2-methylbutanammonium chloride an described in Method B7a. 2,5-methylaniline was converted to 2,5-dimethyl-4-nitrophenyl isothiocyanate according to Method A2a. 2,5-Dimethyl-4-nitrophenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-2-methylbutanammonium chloride to Method C1a to give (4S)-2-(2,5-dimethyl-4-nitrophenylimino)-4-(2-butyl)-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give (4S)-2-(2,5dimethyl-4-nitrophenylimino)-4-butyl-3-isobutyl-1,3-thiazolidine.

Sources & evidence

ORD record
ord-529f0e8b319a433d99dd9e91427ea416
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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