Ethanolamine → HCID 178445849, compound

HRID 276452Notes

Reaction equation

HRID 276452 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.[F:23][C:24]([F:38])([F:37])[C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[N:34]=[C:35]=[S:36]>>[F:38][C:24]([F:37])([F:23])[C:25]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=1[N:34]=[C:35]1[NH:8][C@@H:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[CH2:2][S:36]1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 65105(+)-L-Leucine methyl esterHCID 111307L-LeucinolHCID 18316459HCID 18316459, compound

Product 1

HCID 178445849HCID 178445849, 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-(Trifluoromethyl)4-nitrophenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1c to give (4S)-2-(2-(trifluoromethyl)-4-nitrophenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2f to afford (4S)-2-(2-(trifluoromethyl)-4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine trifluoroacetate salt.

Sources & evidence

ORD record
ord-e73282e7c7654b7eb7f9c60f840c9481
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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