Ethanolamine → HCID 178445842, compound

HRID 276453Notes

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

Participants

Reactant 4

HCID 700Ethanolamine

HCID 65105(+)-L-Leucine methyl ester

HCID 111307L-Leucinol

HCID 183159634-Isothiocyanato-3-(trifluoromethyl)benzonitrile

Product 1

HCID 178445842HCID 178445842, 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. 4-Cyano-2-(trifluoromethyl)phenyl isothiocyanate was reacted with (1S)-1-(chloromethyl)-3-methylbutanammonium chloride according to Method C1c to give (4S)-2-(4-cyano-2-(trifluoromethyl)phenylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2f to afford (4S)-2-(4-cyano-2-(trifluoromethyl)phenylimino)-3,4-diisobutyl-1,3-thiazolidine trifluoroacetate salt.

Sources & evidence

ORD record: ord-78e0a9f0ed654e6aab9187da4be70f17
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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