Ethanolamine → (4S)-2-(4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine

HRID 276472

Reaction equation

OC[C@@H](N)CC(C)C.COC(=O)[C@H](CC(C)C)N.OCCN.[CH3:23][CH:24]([CH3:34])[CH2:25][C@H:26]([NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:27]O.[Cl-].C([NH3+])C(C)C.[N+:41]([C:44]1[CH:49]=[CH:48][C:47]([N:50]=[C:51]=[S:52])=[CH:46][CH:45]=1)([O-:43])=[O:42]>>[N+:41]([C:44]1[CH:45]=[CH:46][C:47]([N:50]=[C:51]2[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C@@H:26]([CH2:25][CH:24]([CH3:34])[CH3:23])[CH2:27][S:52]2)=[CH:48][CH:49]=1)([O-:43])=[O:42]

Participants

Reactant 6

HCID 700Ethanolamine2×

HCID 21133Isobutylaminehydrochloride2×

HCID 65105(+)-L-Leucine methyl ester

HCID 75044Benzene, 1-isothiocyanato-4-nitro-

HCID 111307L-Leucinol

HCID 22951222(2S)-4-methyl-2-(isobutylamino)pentanol

Product 1

HCID 57124422(4S)-2-(4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine

Procedure

(1S)-1-(Hydroxymethyl)-3-methylbutylamine was made from (L)-leucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (2S)-4-methyl-2-(isobutylamino)pentan-1-ol as described in Method B4c. The resulting 2-hydroxyethylamine was converted to N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride according to Method B7c. 4-Nitrophenyl isothiocyanate was reacted with N-(1S)-1-(chloromethyl)-3-methylbutyl)-N-(isobutyl)ammonium chloride to Method C1f to afford (4S)-2-(4-nitrophenylimino)-3,4-diisobutyl-1,3-thiazolidine.

Sources & evidence

ORD record: ord-393b1e9400894e05b8860b5be6f2eaf3
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Linked notes

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