Ethanolamine → HCID 178428753, compound

HRID 276450Notes

Reaction equation

HRID 276450 reaction equation
CO[C:3](=O)[C@H:4]([CH2:6][CH:7]([CH3:9])[CH3:8])[NH2:5].OCCN.[CH3:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[N:25]=[C:26]=[S:27]>>[CH3:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[N:25]=[C:26]1[NH:5][C@@H:4]([CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:3][S:27]1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 65105(+)-L-Leucine methyl esterHCID 1456212-Methyl-4-nitrophenyl isothiocyanate

Product 1

HCID 178428753HCID 178428753, compound

Procedure

(1S)-(Hydroxymethyl)-3-methylbutylamine was made from (L)-leucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (1S)-1-(chloromethyl)-1-methylbutanammonium chloride as described in Method B7a. 2-Methyl-4-nitrophenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1a to give (4S)-2-(2-methyl-4-nitrophenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with 5-iodoheptane according to Method D2a to give (4S)-2-(2-methyl-4-nitrophenylimino)-4-isobutyl-3-(5-heptyl)-1,3-thiazolidine.

Sources & evidence

ORD record
ord-9b580d186e1743d3beace46d7c618254
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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