1-Bromo-2-methylpropane → (4S)-2-(4-nitro-1-naphthylimino)-3,4-diisobutyl1,3-thiazolidine

HRID 276471Notes

Reaction equation

HRID 276471 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([N:14]=[C:15]2[NH:19][C@@H:18]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:17][S:16]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:24](Br)[CH:25]([CH3:27])[CH3:26]>>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([N:14]=[C:15]2[N:19]([CH2:24][CH:25]([CH3:27])[CH3:26])[C@@H:18]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:17][S:16]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 65551-Bromo-2-methylpropaneHCID 178445847HCID 178445847, compound

Product 1

HCID 57275371(4S)-2-(4-nitro-1-naphthylimino)-3,4-diisobutyl1,3-thiazolidine

Procedure

(1S)-1-(Hydroxymethyl)-3-methylbutylamine was made from (L)-leucine methyl ester as described in Method B1b. 4-Nitro-1-naphthylamine was converted to 4-nitro-1-naphthyl isothiocyanate according to Method A2b. 4-Nitro-1-naphthyl isothiocyanate was reacted with (1S)-1-(hydroxymethyl)-3-methylbutylamine to Method C2a to give (4S)-2-(4-nitro-1-naphthylimino)-4-isobutyl-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give (4S)-2-(4-nitro-1-naphthylimino)-3,4-diisobutyl-1,3-thiazolidine.

Sources & evidence

ORD record
ord-a3837cd4472a4746a3f8ae93a624c455
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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