2-Methyl-4-nitrophenyl isothiocyanate → (4S)-2-(2-methyl-4-nitrophenylimino)-4-benzyl-1,3-thiazolidine

HRID 276494Notes

Reaction equation

[CH2:1]([C@H:8]([NH2:11])[CH2:9]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].ClC[C@@H]([NH3+])CC1C=CC=CC=1.[CH3:24][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]>>[CH3:24][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:11][C@@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][S:36]1

Participants

Reactant 3

HCID 1456212-Methyl-4-nitrophenyl isothiocyanate

HCID 447213phenylalaninol, (S)-

HCID 69994545(1S)-2-chloro-1-benzylethylammonium chloride2×

Product 1

HCID 178428750(4S)-2-(2-methyl-4-nitrophenylimino)-4-benzyl-1,3-thiazolidine

Procedure

(1S)-1-Benzyl-2-hydroxyethylamine was converted to (1S)-2-chloro-1-benzylethylammonium chloride according to Method B7b. 2-Methyl-4-nitrophenyl isothiocyanate was reacted with (1S)-2-chloro-1-benzylethylammonium chloride according to Method C1a to give (4S)-2-(2-methyl-4-nitrophenylimino)-4-benzyl -1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford (4S)-2-(2-methyl-4-nitrophenylimino)-4-benzyl-3-isobutyl-1,3-thiazolidine HCl salt.

Sources & evidence

ORD record: ord-8c786e54648547e4985475ba26491c67
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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